[ CAS No. 63132-85-4 ]

Name: 63132-85-4|3-Chloropropane-1-sulfonic acid tert-butylamide|97%
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Product Details of [ 63132-85-4 ]

CAS No. :	63132-85-4	MDL No. :	MFCD11707045
Formula :	C₇H₁₆ClNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SPGDRXRIVPMUCK-UHFFFAOYSA-N
M.W :	213.73	Pubchem ID :	11701296
Synonyms :

Safety of [ 63132-85-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 63132-85-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 63132-85-4 ]
Downstream synthetic route of [ 63132-85-4 ]

[ 63132-85-4 ] Synthesis Path-Upstream 1~1

1
[ 63132-85-4 ]
[ 74-88-4 ]
[ 669008-25-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -69 - 20℃; for 4.33333 h; Stage #2: at -65 - 50℃; for 4.66667 h;	Preparation 16N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide[0072]N-(tert-butyl)-3-chloropropane-1-sulfonamide (Previously dried by azeotroping with 3×100 mL toluene) (100 g, 468 mmol) and THF (1500 mL). This was cooled to an internal temperature of −69° C. then butyl lithium (2.5M in hexanes, 412 mL, 1.02 mol) was added dropwise over a period of 55 min while keeping the internal temperature below −65° C. The ice bath was removed and the reaction mixture was warmed to rt over 1.5 h and then cooled back down to an internal temperature of −69° C. Butyl lithium (196 mL, 515 mmol) was added to the reaction mixture over a period of 25 min while keeping the internal temperature below −65° C. The reaction mixture was then warmed to rt over the course of 1.5 h. The reaction mixture was recooled to an internal temperature of −69° C. and iodomethane (58.5 mL, 936 mmol) was added dropwise over a period of 40 min while keeping the internal temperature below −65° C. The reaction mixture was then warmed to an internal temperature of −50° C. over the course of 4 h. The cold bath was removed and a solution of saturated NH₄Cl (1000 mL) was added. The quenched reaction mixture was transferred to a separatory funnel along with ethyl acetate (100 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. (3×75 mL). The combined organic layers were washed with brine (700 mL), dried with MgSO₄, and concentrated in vacuo to an off white solid which was dried under high vac for 30 min to yield N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide as a white solid (88.5 g, 99percent yield). ¹H NMR (500 MHz, CDCl₃) δ 4.07 (bs, 1H), 1.51 (s, 3H), 1.38-1.41 (m, 2H), 1.36 (s, 9H), 0.77-0.80 (m, 2H).
99%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -69 - 20℃; for 4.33333 h; Stage #2: at -69 - -50℃; for 4.66667 h;	Preparation 16 N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide [0104] N-(tert-butyl)-3-chloropropane-1-sulfonamide (Previously dried by azeotroping with 3 x 1OOmL toluene) (100 g, 468 mmol) and THF (1500 niL). This was cooled to an internal temperature of -69 °C then butyl lithium (2.5M in hexanes, 412 mL, 1.02 mol) was added dropwise over a period of 55 min while keeping the internal temperature below -65 °C. The ice bath was removed and the reaction mixture was warmed to rt over 1.5 h and then cooled back down to an internal temperature of -69 °C. Butyl lithium (196 mL, 515 mmol) was added to the reaction mixture over a period of 25 min while keeping the internal temperature below -65 °C. The reaction mixture was then warmed to rt over the course of 1.5h. The reaction mixture was recooled to an internal temperature of -69 °C and iodo methane (58.5 mL, 936 mmol) was added dropwise over a period of 40 min while keeping the internal temperature below-65 °C. The reaction mixture was then warmed to an internal temperature of -50 °C over the course of 4h. The cold bath was removed and a solution of saturated NH4C1 (1000 mL) was added. The quenched reaction mixture was transferred to a separatory funnel along with ethyl acetate (100 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. (3 x 75 mL). The combined organic layers were washed with brine (700 mL), dried with MgS04, and concentrated in vacuo to an off white solid which was dried under high vac for 30 min to yield N-(tert-butyl)-1-methylcyclopropane-1 -sulfonamide as a white solid (88.5 g, 99percent yield). NMR (500 MHz, CDC13) δ 4.07 (bs, 1 H), 1.51 (s, 3 H), 1.38-1.41 (m, 2 H), 1.36 (s, 9 H), 0.77-0.80 (m, 2 H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at 20℃; Neat (no solvent)	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).

81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at -78 - 20℃;	A solution of N-tert-Butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyliodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1 H)
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at 20℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at 20℃;	A solution of N-tert-Butyl- (3-chloro) propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to-78 °C. To this solution was added n- BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to-78°C, and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to-78 °C over a period of 2 h and a neat solution of methyliodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgS04), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent) :'H NMR (CDCl3) 8 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H)
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at -78 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane at 20℃;	Step Ib. Preparation ofN-tert-Butyl-(l-methyl)cyclopropylsulfonamide.; A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to - 78 ⁰C. To this solution was added n- BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5h. This mixture was then cooled to - 78°C, and a solution of M-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 ⁰C over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated <n="54"/>NH₄Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO₄), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, IH).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at -78 - 20℃;	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH₄Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO₄), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at -78 - 20℃;	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH₄Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO₄), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Stage #2: at 20℃;	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5 h; Stage #2: at 20℃; Neat (no solvent)	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: at -78 - 20℃;	Step 2: Preparation of N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide A solution of the product of Step 1 (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-butyllithium (17.6 mL, 44 mmol, 2.5M in hexane) slowly. The dry ice bath was removed and the reaction mixture was warmed to room temperature over a period of 1.5 hours. This mixture was cooled to -78° C. and a solution of n-butyllithium (20 mmol, 8 mL, 2.5M in hexane) was added. The reaction mixture was warmed to room temperature, cooled to -78° C. over a period of 2 hours, and treated with a neat solution of methyl iodide (5.68 g, 40 mmol). The reaction mixture was warmed to room temperature overnight, then quenched with saturated NH₄Cl (100 mL) at room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO₄), filtered, and concentrated in vacuo to provide a yellow oil which was crystallized from hexane to provide the desired product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (br s, 1H).
81%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3.5 h; Cooling with dry ice Stage #2: at -78 - 20℃;	A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to - 78 ⁰C. To this solution was added n- <n="52"/>BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5h. This mixture was then cooled to - 78°C, and a solution of M-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 ⁰C over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH₄Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO₄), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81percent): ¹H NMR (CDCl₃) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, IH).

Reference： [1] Patent: US2013/102589, 2013, A1, . Location in patent: Paragraph 0072; 0073
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[ 63132-85-4 ] Synthesis Path-Downstream 1~17

1
[ 63132-85-4 ]
N-t-butyl-1-cyclopropylsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3h;	A.II.7.B.3 A solution of n-BuLi (86.7 mL, 138.8 mmol, 1.6 M in hexane) was dissolved in dry THF (120 mL) and cooled to -78° C. under a argon atmosphere. To this solution was added a solution of N-tert-butyl-(3-chloro)propylsulfonamide from Step B.2 (14.5 g, 67.8 mmol) in dry THF (160 mL) slowly dropwise over 60 minutes. The dry ice bath was removed and the reaction mixture was allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with glacial acetic acid (3.4 mL), concentrated in vacuo, and partitioned between CH2Cl2 (100 mL) and water (100 mL). The organic phase was washed with aqueous 1N NaOH (150 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the N-tert-Butyl cyclopropylsulfonamide as a waxy off white solid (12 g, 100%): 1H NMR (CDCl3) δ 0.98 (m, 2H), 1.17 (m, 2H), 1.38 (s, 9H), 2.45 (m, 1H), 4.45 (br s, 1H). 13C NMR (CDCl3) δ 6.5, 30.6, 33.5, 54.2. MS (ESI) 176 (M+-H).
100%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 3h;	A.B.i A solution of n-BuLi (86.7 mL, 138.8 mmol, 1.6 M in hexane) was dissolved in dry TBF (120 mL) and cooled to -78° C. under a Argon atmosphere. To this solution was added a solution of N-tert-Butyl-(3-chloro)propylsulfonamide from Step 1a,(14.5 g, 67.8 mmol) in dry THF (160 mL 15, slowly dropwise over 60 min. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 2 h. The reaction mixture was quenched with glacial AcOH (3.4 mL), concentrated in vacuo, and partitioned between CH2Cl2 (100 mL) and water (100 mL). The organic phase was washed with aqueous 1N NaOH (150 mL), brine (100 mL), dried (MgSO4), and concentrated in vacuo to afford the N-tert-Butyl cyclopropylsulfonamide as a waxy offwhite solid (12 g, 100%): 1H NMR (CDCl3) δ 0.98 (m, 2H), 1.17 (m, 2H), 1.38 (s, 9H), 2.45 (m, 1 H), 4.45 (bs, 1 H). 13C NMR (CDCl3) δ 6.5, 30.6, 33.5, 54.2. MS (ESI) 176 (M+-H).
96%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 4h; Stage #2: With water; ammonium chloride In tetrahydrofuran at 0℃;	2D.2 Step 2:; A dry 5 L 3-neck flask equipped with a magnetic stir bar, argon inlet and 2addition funnels was flushed with argon and anhydrous THF (1 .5 L) was transferredinto the flask via cannula and cooled to -78°C. Compound 2d2 (96.73 g, 0.453 mol,1.0 eq) was dissolved in anhydrous THF (390 rtiL) and the solution was transferredinto one of the addition funnels. n-Butyllithium solution (2.5 M in hexanes, 390 ml_,0.975 mol, 2.15 eq) was transferred to the other addition funnel and the solutions inthe addition funnels were added to the flask simultaneously over 4 hours. Whenaddition was complete, the mixture was allowed to warm to room temperature. Oncethe internal temperature reached ~0°C, the reaction was quenched by dropwiseaddition of saturated NH4CI solution (200 ml_). The THF was removed under vacuumand the residue was diluted with CH2CI2 (2 L) and water (1 L). The layers wereseparated and the organic layer was washed with water (2 x 1 L) and brine (800 ml_),dried over sodium sulfate, filtered and evaporated to dryness. Compound 2d3 wasobtained as an orange-beige solid (77.32 g, 96% yield). 1H NMR (CDCI3, 400 MHz): 84.25 (s, 1H), 2.48 (m, 1H), 1.42 (s, 9H), 1.19 (m), 1.01 (m).

96%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 4h; Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water at 0℃;	2D.2 A dry 5 L 3-neck flask equipped with a magnetic stir bar, argon inlet and 2 addition funnels was flushed with argon and anhydrous THF (1.5 L) was transferred into the flask via cannula and cooled to -78° C. Compound 2d2 (96.73 g, 0.453 mol, 1.0 eq) was dissolved in anhydrous THF (390 mL) and the solution was transferred into one of the addition funnels. n-Butyllithium solution (2.5 M in hexanes, 390 mL, 0.975 mol, 2.15 eq) was transferred to the other addition funnel and the solutions in the addition funnels were added to the flask simultaneously over 4 hours. When addition was complete, the mixture was allowed to warm to room temperature. Once the internal temperature reached 0° C., the reaction was quenched by dropwise addition of saturated NH4Cl solution (200 mL). The THF was removed under vacuum and the residue was diluted with CH2Cl2 (2 L) and water (1 L). The layers were separated and the organic layer was washed with water (2×1 L) and brine (800 mL), dried over sodium sulfate, filtered and evaporated to dryness. Compound 2d3 was obtained as an orange-beige solid (77.32 g, 96% yield). 1H NMR (CDCl3, 400 MHz): δ4.25 (s,1H), 2.48 (m,1H), 1.42 (s, 9H), 1.19 (m), 1.01 (m).
96%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4h; Stage #2: With water; ammonium chloride In tetrahydrofuran; hexane at 0℃;	4A.B Step B; A dry 5 L 3-neck flask equipped with a magnetic stir bar, argon inlet and 2 addition funnels was flushed with argon and anhydrous THF (1.5 L) was transferred into the flask via cannula and cooled to -78°C. Compound 4A2 (96.73 g, 0.453 mol, 1.0 eq) was dissolved in anhydrous THF (390 ml_) and the solution was transferred into one of the addition funnels. n-Butyllithium solution (2.5 M in hexanes, 390 ml_, 0.975 mol, 2.15 eq) was transferred to the other addition funnel and the solutions in the addition funnels were added to the flask simultaneously over 4 hours. When addition was complete, the mixture was allowed to warm to room temperature. Once the internal temperature reached ~0°C, the reaction was quenched by dropwise addition of saturated NH4CI solution (200 ml_). The THF was removed under vacuum and the residue was diluted with CH2CI2 (2 L) and water (1 L). The layers were separated and the organic layer was washed with water (2 x 1 L) and brine (800 mL), dried over sodium sulfate, filtered and evaporated to dryness. Compound 4A3 was obtained as an orange-beige solid (77.32 g, 96% yield). 1H NMR (CDCI3, 400 MHz): δ 4.25 (s, 1 H), 2.48 (m, 1 H), 1.42 (s, 9H), 1.19 (m), 1.01 (m).
94%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h;
88%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
56%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Stage #2: With water In ethyl acetate	A.II.1.2.2 Step 2: Preparation of Cyclopropanesulfonic acid tert-butylamide To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-butyllithium (2.5M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reation mixture was allowed to warm up to room temperature over period of 1 hour. The volatiles were removed in vacuo. The residue was partitioned between ethyl acetate and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (in, 1H), 4.19 (br, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane	O.12.2 Step 2 Step 2 Preparation of Cyclopropanesulfonic Acid tert-butylamide To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reation mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 11H), 4.19 (b, 11H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	A.II.2.2 Preparation of Cyclopropanesulfonic Acid Tert-Butylamide To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-butyllithium (2.5M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reaction mixture was warmed to room temperature over a period of 1 hour and concentrated in vacuo. The concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The concentrate was recrystallized from hexane to provide the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (br, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h;	4.B.2 To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	A.II.1.2 Step 2: preparation of Cyclopropanesulfonic acid tert-butylamide To a solutionof N-tert-butyl- (3-chloro) propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0mmol) at-78 C. The reation mixture was allowed to warm up to room temperature over period of1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g,56%). 'H NMR(CDC13)8 0.98-1. 00 (m, 2H), 1.18-1. 19 (m, 2H), 1.39 (s, 9H), 2.48-2. 51 (m,1H), 4.19 (b,lH).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	A.III.1.2 To a solution of N-tert-butyl- (3-chloro) propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at-78°C. The reation mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 'H NMR (CDC13) 8 0.98-1. 00 (m, 2H), 1.18-1. 19 (m, 2H), 1.39 (s, 9H), 2. 48-2.51 (m, 1H), 4.19 (b, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	6.B.2 Step 2: Preparation of Cyclopropanesulfonic acid tert-butylamide; To a solution ofN-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) inTHF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -780C.The reation mixture was allowed to warm up to room temperature over period of 1 h.The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51(m, IH), 4.19 (b, IH).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	6.B.2 To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reation mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	4.B.2 Step 2: Preparation of Cyclopropanesulfonic acid tert-butylamide To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reation mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H). A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	4.B.2 To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	4.B.2 To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1 - 1.5h;	I.1.1.2; I.2.2a.2 Step 2:; To a solution of the product of Step 1 (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 hour and concentrated in vacuo. The residue was partitioned between ethyl acetate and water (200 mL each). The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was recrystallized from hexane to provide the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (b, 1H).; Step 2: Preparation of N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide; A solution of the product of Step 1 (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78° C. To this solution was added n-butyllithium (17.6 mL, 44 mmol, 2.5M in hexane) slowly. The dry ice bath was removed and the reaction mixture was warmed to room temperature over a period of 1.5 hours. This mixture was cooled to -78° C. and a solution of n-butyllithium (20 mmol, 8 mL, 2.5M in hexane) was added. The reaction mixture was warmed to room temperature, cooled to -78° C. over a period of 2 hours, and treated with a neat solution of methyl iodide (5.68 g, 40 mmol). The reaction mixture was warmed to room temperature overnight, then quenched with saturated NH4Cl (100 mL) at room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil which was crystallized from hexane to provide the desired product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (br s, 1H).
56%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	6.B.2 To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) inTHF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at -780C.The reation mixture was allowed to warm up to room temperature over period of 1 h.The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51(m, IH), 4.19 (b, IH).
	With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 0℃; for 0.5h;	1; 2 EXAMPLE 1 To a solution of 36.6 g (0.50 mol) tert-butylamine and 50.4 g (0.50 mol) triethylamine in 400 mL of toluene cooled to 0° C. to 5° C. was added 3-chloropropane sulfonyl chloride (73.0 g, 0.41 mol) within 30 to 60 minutes and the resulting mixture was stirred at 5° C. for 10 min. The mixture was warmed to room temperature and treated with 200 mL of 1 M hydrochloric acid. The layers were allowed to separate and the aqueous layer was removed. The organic layer was washed with water (1100 mL). From the organic layer approx. 250 mL of toluene were distilled off. THF (700 mL) was added and distillation was continued until the residual volume in the reaction vessel was approx. 600 mL. The mixture was cooled to -30° C. and 385 g of BuLi (15% in hexane, 2.2 eq) was added. After 30 min at -30° C. the mixture was warmed to 0° C. treated with water (200 mL). The layers were allowed to separate. The aqueous layer was removed and the organic layer was washed with water (1100 mL) and concentrated. The residue was treated with formic acid (300 mL) at 80° C. for 20 h. During the entire reaction a slight stream of nitrogen was bubbled through the solution. After complete conversion the mixture was concentrated to dryness. Residual amounts of formic acid were removed by co-evaporation with toluene (2*250 mL). The remaining residue was treated with toluene (100 mL) and ethanol (35 mL), heated to 70 to 75° C. and stirred at this temperature until a clear solution was obtained. The solution was cooled to 50° C. and treated at this temperature with 300 mL of toluene. The mixture was then cooled to -10 to -15° C. and stirred at this temperature for 5 h. The crystals were filtered off, washed with 50 ml of pre-cooled toluene and dried at 50° C./<30 mbar to afford 34.5 g (69.9%) of cyclopropyl sulfonamide as colorless crystals with a purity of 99.8% (GC, % area). EXAMPLE 2To a solution of 18.3 g (0.25 mol) tert-butylamine and 25 g (0.25 mol) triethylamine in 200 mL of toluene cooled to 10° C. to 20° C. was added 3-chloropropane sulfonyl chloride (36.0 g, 0.21 mol) within 30 to 60 minutes and the resulting mixture was stirred at 15° C. for 30 min. The mixture was treated with 90 mL of 1M hydrochloric acid. The layers were allowed to separate and the aqueous layer was removed. The organic layer was washed with water (1×50 mL). From the organic layer toluene was distilled off and replaced by THF. The resulting mixture (150 mL) was cooled to -25° C. and treated at this temperature with 210 g (0.49 mol) of BuLi (15% in hexane). After 30 min at -25° C. the mixture was warmed to 0° C. and treated with water (100 mL). The layers were allowed to separate. The organic layer was washed with water (4×100 mL). The combined aqueous layers were treated with 37% hydrochloric acid (32 mL) and then extracted with toluene (2×100 mL). The combined organic layers were concentrated to a residual volume of 200 mL and then washed with water (2×20 mL). The organic layer was concentrated to dryness. The residue was treated with formic acid (135 mL) and water (15 mL) at 80° C. for 7 h. During the entire reaction a slight stream of nitrogen was bubbled through the solution. After complete conversion the mixture was concentrated to dryness. Residual amounts of formic acid were removed by co-evaporation with toluene (2×100 mL). The resulting residue was dissolved in ethanol (60 mL) at 64° C. and treated with 1.0 g of charcoal. The charcoal was filtered off and washed with ethanol (20 mL). The mixture was heated to reflux temperature and concentrated to a residual volume of approximately 40 mL. The solution was then treated within 30 min at 70° C. with toluene (125 mL). The mixture was cooled to -10° C. within 4 h and stirred at this temperature for 5 h. The crystals were filtered off, washed with 40 mL of pre-cooled toluene and dried at 50° C./<30 mbar to afford 18.73 g (75%) of cyclopropyl sulfonamide as colorless crystals with a purity of 99.9% (GC, % area).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/10455, 2007, A1 Location in patent: Page/Page column 26
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/77551, 2004, A1 Location in patent: Page/Page column 33
[3]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2006/7700, 2006, A1 Location in patent: Page/Page column 79-80
[4]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2006/19905, 2006, A1 Location in patent: Page/Page column 35
[5]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2007/9227, 2007, A1 Location in patent: Page/Page column 42
[6]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]
[7]Milanole, Gaëlle; Andriessen, Floris; Lemonnier, Gérald; Sebban, Muriel; Coadou, Gaël; Couve-Bonnaire, Samuel; Bonfanti, Jean-François; Jubault, Philippe; Pannecoucke, Xavier [Organic Letters, 2015, vol. 17, # 12, p. 2968 - 2971]
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2006/183694, 2006, A1 Location in patent: Page/Page column 25
[9]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/48802, 2004, A1
[10]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/14173, 2008, A1 Location in patent: Page/Page column 26-27
[11]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/107625, 2008, A1 Location in patent: Page/Page column 25
[12]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2003/99274, 2003, A1 Location in patent: Page 64
[13]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2005/51410, 2005, A1 Location in patent: Page/Page column 77-78
[14]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2008/64061, 2008, A1 Location in patent: Page/Page column 51
[15]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/93414, 2007, A1 Location in patent: Page/Page column 26; 39
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2
[ 63132-85-4 ]
[ 93-58-3 ]
[ 669008-31-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: benzoic acid methyl ester In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

3
[ 63132-85-4 ]
[ 75-77-4 ]
[ 888706-09-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

4
[ 63132-85-4 ]
[ 16400-32-1 ]
1-pent-2-ynyl-cyclopropanesulfonic acid tert-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: 1-bromo-pent-2-yne In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

5
[ 63132-85-4 ]
[ 108-94-1 ]
[ 669008-29-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: cyclohexanone In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

6
[ 63132-85-4 ]
[ 100-39-0 ]
[ 669008-33-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: benzyl bromide In tetrahydrofuran; hexane
66.4%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In hexane at -78 - 20℃; for 4.25h; Stage #2: benzyl bromide In tetrahydrofuran; hexane at 20℃; for 8.25h;	C.200.1 A solution of 3-chloro-propane-1-sulfonic acid tert-butylamide (9.34 g, 43.7 mmol) was chilled to-78 °C and treated with 2. 5M n-butyllithium in hexanes (36.7 mL, 92 mmol) dropwise over 20 min. The mixture was stirred for an additional 10 min and was then allowed to warm to rt and stirred for 1.5 h. The mixture was then recooled to-78 °C and was again treated with 2. 5M n-butyllithium in hexanes (19.2 mL, 48 mmol) dropwise over 15 min. The mixture was allowed to warm to rt and stirred for 2 h. The solution was again cooled to-78 °C and was treated with a solution of benzyl bromide (9.71 g, 56. 8 mmol) in dry THF (10 mL) dropwise over 15 min. The mixture was then stirred at rt for 18 h. Saturated aqueous ammonium chloride (50 mL) was added, and the mixture was concentrated in vacuo. To the residue was added ethyl acetate (300 mL) and water (100 mL). The resulting bilayer was shaken and the two phases were separated. The organic phase was washed with water (2 x 100 mL) and brine (50 mL). The combined aqueous washes were back-extracted with ethyl acetate (150 mL), and the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo to give a waxy brown oil. Purification of the crude product by silica gel chromatography (10% ethyl acetate in hexanes) gave the desired product as a white powder (7.75 g, 66.4% yield) : 1H NMR (CDC13) 8 0.72-0. 74 (m, 2 H), 1.26 (s, 9 H), 1.34-1. 36 (m, 2 H), 3.26 (s, 2 H), 3.69 (s, 1 H), 7.19 (d, J=6. 71 Hz, 2 H), 7.23-7. 26 (m, 1 H), 7.29-7. 31 (m, 2 H); MS m/z 290 ).

7
[ 63132-85-4 ]
[ 100-52-7 ]
1-(hydroxy-phenyl-methyl)-cyclopropanesulfonic acid tert-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: benzaldehyde In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

8
[ 63132-85-4 ]
[ 103-71-9 ]
[ 669008-35-9 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: phenyl isocyanate In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

9
[ 63132-85-4 ]
[ 123-38-6 ]
1-(1-hydroxy-propyl)-cyclopropanesulfonic acid tert-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: propionaldehyde In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

10
[ 1633-82-5 ]
[ 75-64-9 ]
[ 63132-85-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	In tetrahydrofuran at 20℃; for 24h;
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	A.II.1.2.1 Method 2 (of 2): Step 1: Preparation of N-tert-butyl-(3-chloro)propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (2.0 L). The resulting solution was washed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (br, 1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	A.II.7.B.2 B.2) Preparation of N-tert-Butyl-(3-chloro)propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. The mixture was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).

99%	In tetrahydrofuran; dichloromethane	O.12.1 Step 1 Step 1 Preparation of N-tert-Butyl-(3-chloro)propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	A.II.2.1 Preparation of N-tert-butyl-(3-chloro)propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. and treated slowly with 3-chloropropanesulfonyl chloride (1.5 mol, 182.4 mL). The reaction mixture was warmed to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2.0 L), washed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L), dried over Na2SO4, filtered, and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the desired product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (br, 1H).
99%	In tetrahydrofuran at -200 - 20℃; for 24h;	4.B.1 tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -200 C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at 20℃; for 24h;	A.II.1.1 1. Preparation of cyclopropylsulfonamide; Step 1: Preparationof N-tert-Butyl- (3-chloro) propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooledto-20 C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved inCH2CI2 (2.0 L). The resulting solution was washed with1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). *'H NMR(CDC13)8 1.38 (s, 9H), 2.30-2. 27 (m, 2H), 3.22 (t, J = 7.35 Hz,2H), 3.68 (t,J = 6.2 Hz, 2H), 4.35 (b,1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	A.I.a Method I (Steps a-d). Preparation of 1-Substituted Cyclopropanesulfonamides Required for N-acylsulfonamide Coupling Steps 3e-8e (Examples 3-8 used to Prepare Compounds 1-6 Respectively). Step Ia: N-tert-Butyl-(3-chloro)propylsulfonamide. Step Ia) A neat solution of tert-Butylamine (315.3 mL, 3.0 mol) was dissolved in THF (2.5 L), cooled to -20° C., and 3-Chloropropanesulfonyl chloride (182.4 mL, 1.5 mol) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%): 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (bs, 1 H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	A.III.1.1 tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to-20°C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2C12 (2.0 L). The resulting solution was washed with 1 N HC1 (1.0 L), water (1. 0 L), brine (1.0 L) and dried over Na2S04. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 'H NMR (CDC13) 8 1. 38 (s, 9H), 2.30-2. 27 (m, 2H), 3.22 (t, J= 7.35 Hz, 2H), 3.68 (t, J= 6. 2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	6.B.1 METHOD B:; Step 1: Preparation ofN-tert-Butyl-(3-chloro)propylsulfonamide; tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to - 200C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J= 7.35 Hz, 2H), 3.68 (t, J= 6.2 Hz, 2H), 4.35 (b, IH).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	6.B.1; 7.1a tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	4.B.1 Step 1: Preparation of N-tert-Butyl-(3-chloro)propylsulfonamide tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -200 - 20℃; for 24h;	4.B.1 tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -200 C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -200 - 20℃; for 24h;	4.B.1 tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to -200C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	I.1.1.1; I.2.2a.1 I. Preparation of P1' Intermediates; 1. Preparation of Cyclopropylsulfonamide; Method 1:; Step 1:; tert-Butylamine (3.0 mol, 315 mL) was dissolved in THF (2.5 L). The solution was cooled to -20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1.0M HCl (1.0 L), water (1.0 L), and brine (1.0 L), dried over Na2SO4, filtered, and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (b, 1H).; 2. Preparation of C1-Substituted Cyclopropylsulfonamides; 2a. Preparation of N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide; Step 1: Preparation of N-tert-butyl-(3-chloro)propylsulfonamide; Prepared as described above.
99%	In tetrahydrofuran at -20 - 20℃; for 24h;	6.B.1; 7.1.a tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to - 200C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2CI2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J= 7.35 Hz, 2H), 3.68 (t, J= 6.2 Hz, 2H), 4.35 (b, IH).
97%	In dichloromethane at 20℃; Cooling with ice-water bath;	41 3-Chloro-N-(1,1-dimethylethyl)-1-propanesulfonamide 3-Chloro-N-(1,1-dimethylethyl)-1-propanesulfonamide To a solution of 3-chloropropanesulfonyl chloride (commercially available, for example, from Aldrich) (1 g, 6 mmol) in DCM (10 ml) in an ice-water bath was added t-butylamine (commercially available, for example, from Aldrich) (1.3 ml, 12 mmol). The solution was allowed to warm to ambient temperature and stirred for 3 h. The reaction mixture was applied to a SCX-2 cartridge (50 g) (preconditioned with methanol) and the cartridge eluted with methanol (2 column volumes). The methanol fraction was concentrated in vacuo to give the title compound as a white waxy solid (1.17 g, 97%). LCMS RT=2.61 min, ES+ve m/z 214 (M+H)+.
88%	With triethylamine In dichloromethane at 0℃; for 1.75h;	2D.1 Step 1 :; A dry 3 L 3-neck flask equipped with a magnetic stir bar, addition funnel andargon inlet was flushed with argon, then charged with 3-chloropropanesulfonylchloride 2d1 (100.48 g, 0.57 mol, 1 .0 eq). Anhydrous dichloromethane (900 ml_) wastransferred into the flask via cannula, the mixture was cooled in an ice/water bath andtert-butylamine (72 ml_, 0.68 mol, 1.2 eq) was added. The mixture was stirred 15minutes then a solution of triethylamine (158 ml, 1.13 mol, 2.0 eq) in anhydrousdichloromethane (100 ml) was added dropwise over 45 minutes and stirring was 'continued for 1 h. The mixture was diluted with dichloromethane (500 ml_) andwashed with 1N HCI (3 x 400 ml_) and brine. The organic layer was dried over sodiumsulfate, filtered and evaporated to dryness to give compound 2d2 as an orange-beigesolid (107.04 g, 88% yield). 1H NMR (CDCI3, 400 MHz): 84.46 (s, 1H), 3.71 (tr, 2H),3.25 (tr, 2H), 2.31 (m, 2H), 1.41 (s, 9H).
88%	Stage #1: 3-chloro-n-propanesulfonyl chloride; <i>tert</i>-butylamine In dichloromethane at 0℃; for 0.25h; Stage #2: With triethylamine In dichloromethane for 1.75h;	2D.1 A dry 3 L 3-neck flask equipped with a magnetic stir bar, addition funnel and argon inlet was flushed with argon, then charged with 3-chloropropanesulfonyl chloride 2d1 (100.48 g, 0.57 mol, 1.0 eq). Anhydrous dichloromethane (900 mL) was transferred into the flask via cannula, the mixture was cooled in an ice/water bath and tert-butylamine (72 mL, 0.68 mol, 1.2 eq) was added. The mixture was stirred 15 minutes then a solution of triethylamine (158 mL, 1.13 mol, 2.0 eq) in anhydrous dichloromethane (100 mL) was added dropwise over 45 minutes and stirring was continued for 1 h. The mixture was diluted with dichloromethane (500 mL) and washed with 1 NHCl (3×400 mL) and brine. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness to give compound 2d2 as an orange-beige solid (107.04 g, 88% yield). 1H NMR (CDCl3, 400 MHz): δ4.46 (s,1H), 3.71 (tr, 2H), 3.25 (tr, 2H), 2.31 (m, 2H), 1.41 (s, 9H).
88%	With triethylamine In dichloromethane at 0℃; for 2h;	4A.A EXAMPLE 4A; Preparation of PV fragments Cyclopropylsulfonamide (4A4) and 1- methylcyclopropylsulfonamide (4A7); Cyclopropanesulfonamide can be prepared by amination of cyclopropanesulfonyl chloride, according to the literature reference of J. King et al., J. Org. Chem., 1993, 58, 1128-1135, or as set out below.; Step A; A dry 3 L 3-neck flask equipped with a magnetic stir bar, addition funnel and argon inlet was flushed with argon, then charged with 3-chloropropanesulfonyl chloride 4A1 (100.48 g, 0.57 mol, 1.0 eq). Anhydrous dichloromethane (900 mL) was transferred into the flask via cannula, the mixture was cooled in an ice/water bath and tert- butylamine (72 mL, 0.68 mol, 1.2 eq) was added. The mixture was stirred 15 minutes then a solution of triethylamine (158 mL, 1.13 mol, 2.0 eq) in anhydrous dichloromethane (100 mL) was added dropwise over 45 minutes and stirring was continued for 1 h. The mixture was diluted with dichloromethane (500 mL) and washed with 1 N HCI (3 x 400 mL) and brine. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness to give compound 4A2 as an orange-beige solid (107.04 g, 88% yield). 1H NMR (CDCI3, 400 MHz): 54.46 (s, 1H), 3.71 (tr, 2H), EPO 3.25 (tr, 2H), 2.31 (m, 2H), 1.41 (s, 9H).
83%	In tetrahydrofuran at -20 - 20℃; for 24h; Inert atmosphere;
	Stage #1: 3-chloro-n-propanesulfonyl chloride; <i>tert</i>-butylamine With triethylamine In toluene at 0 - 20℃; for 0.666667 - 1.5h; Stage #2: With hydrogenchloride In water; toluene	1; 2 EXAMPLE 1 To a solution of 36.6 g (0.50 mol) tert-butylamine and 50.4 g (0.50 mol) triethylamine in 400 mL of toluene cooled to 0° C. to 5° C. was added 3-chloropropane sulfonyl chloride (73.0 g, 0.41 mol) within 30 to 60 minutes and the resulting mixture was stirred at 5° C. for 10 min. The mixture was warmed to room temperature and treated with 200 mL of 1 M hydrochloric acid. The layers were allowed to separate and the aqueous layer was removed. The organic layer was washed with water (1100 mL). From the organic layer approx. 250 mL of toluene were distilled off. THF (700 mL) was added and distillation was continued until the residual volume in the reaction vessel was approx. 600 mL. The mixture was cooled to -30° C. and 385 g of BuLi (15% in hexane, 2.2 eq) was added. After 30 min at -30° C. the mixture was warmed to 0° C. treated with water (200 mL). The layers were allowed to separate. The aqueous layer was removed and the organic layer was washed with water (1100 mL) and concentrated. The residue was treated with formic acid (300 mL) at 80° C. for 20 h. During the entire reaction a slight stream of nitrogen was bubbled through the solution. After complete conversion the mixture was concentrated to dryness. Residual amounts of formic acid were removed by co-evaporation with toluene (2*250 mL). The remaining residue was treated with toluene (100 mL) and ethanol (35 mL), heated to 70 to 75° C. and stirred at this temperature until a clear solution was obtained. The solution was cooled to 50° C. and treated at this temperature with 300 mL of toluene. The mixture was then cooled to -10 to -15° C. and stirred at this temperature for 5 h. The crystals were filtered off, washed with 50 ml of pre-cooled toluene and dried at 50° C./<30 mbar to afford 34.5 g (69.9%) of cyclopropyl sulfonamide as colorless crystals with a purity of 99.8% (GC, % area). EXAMPLE 2To a solution of 18.3 g (0.25 mol) tert-butylamine and 25 g (0.25 mol) triethylamine in 200 mL of toluene cooled to 10° C. to 20° C. was added 3-chloropropane sulfonyl chloride (36.0 g, 0.21 mol) within 30 to 60 minutes and the resulting mixture was stirred at 15° C. for 30 min. The mixture was treated with 90 mL of 1M hydrochloric acid. The layers were allowed to separate and the aqueous layer was removed. The organic layer was washed with water (1×50 mL). From the organic layer toluene was distilled off and replaced by THF. The resulting mixture (150 mL) was cooled to -25° C. and treated at this temperature with 210 g (0.49 mol) of BuLi (15% in hexane). After 30 min at -25° C. the mixture was warmed to 0° C. and treated with water (100 mL). The layers were allowed to separate. The organic layer was washed with water (4×100 mL). The combined aqueous layers were treated with 37% hydrochloric acid (32 mL) and then extracted with toluene (2×100 mL). The combined organic layers were concentrated to a residual volume of 200 mL and then washed with water (2×20 mL). The organic layer was concentrated to dryness. The residue was treated with formic acid (135 mL) and water (15 mL) at 80° C. for 7 h. During the entire reaction a slight stream of nitrogen was bubbled through the solution. After complete conversion the mixture was concentrated to dryness. Residual amounts of formic acid were removed by co-evaporation with toluene (2×100 mL). The resulting residue was dissolved in ethanol (60 mL) at 64° C. and treated with 1.0 g of charcoal. The charcoal was filtered off and washed with ethanol (20 mL). The mixture was heated to reflux temperature and concentrated to a residual volume of approximately 40 mL. The solution was then treated within 30 min at 70° C. with toluene (125 mL). The mixture was cooled to -10° C. within 4 h and stirred at this temperature for 5 h. The crystals were filtered off, washed with 40 mL of pre-cooled toluene and dried at 50° C./<30 mbar to afford 18.73 g (75%) of cyclopropyl sulfonamide as colorless crystals with a purity of 99.9% (GC, % area).

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[ 63132-85-4 ]
[ 106-95-6 ]
[ 669008-27-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide With n-butyllithium In tetrahydrofuran; hexane Stage #2: allyl bromide In tetrahydrofuran; hexane

Reference： [1]Li, Jianqing; Smith, Daniel; Wong, Henry S.; Campbell, Jeffrey A.; Meanwell, Nicholas A.; Scola, Paul M. [Synlett, 2006, # 5, p. 725 - 728]

12
[ 63132-85-4 ]
[ 74-88-4 ]
[ 669008-25-7 ]

Yield	Reaction Conditions	Operation in experiment
99%		Preparation 16N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide[0072]N-(tert-butyl)-3-chloropropane-1-sulfonamide (Previously dried by azeotroping with 3×100 mL toluene) (100 g, 468 mmol) and THF (1500 mL). This was cooled to an internal temperature of -69 C. then butyl lithium (2.5M in hexanes, 412 mL, 1.02 mol) was added dropwise over a period of 55 min while keeping the internal temperature below -65 C. The ice bath was removed and the reaction mixture was warmed to rt over 1.5 h and then cooled back down to an internal temperature of -69 C. Butyl lithium (196 mL, 515 mmol) was added to the reaction mixture over a period of 25 min while keeping the internal temperature below -65 C. The reaction mixture was then warmed to rt over the course of 1.5 h. The reaction mixture was recooled to an internal temperature of -69 C. and iodomethane (58.5 mL, 936 mmol) was added dropwise over a period of 40 min while keeping the internal temperature below -65 C. The reaction mixture was then warmed to an internal temperature of -50 C. over the course of 4 h. The cold bath was removed and a solution of saturated NH4Cl (1000 mL) was added. The quenched reaction mixture was transferred to a separatory funnel along with ethyl acetate (100 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. (3×75 mL). The combined organic layers were washed with brine (700 mL), dried with MgSO4, and concentrated in vacuo to an off white solid which was dried under high vac for 30 min to yield N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide as a white solid (88.5 g, 99% yield). 1H NMR (500 MHz, CDCl3) delta 4.07 (bs, 1H), 1.51 (s, 3H), 1.38-1.41 (m, 2H), 1.36 (s, 9H), 0.77-0.80 (m, 2H).
99%		Preparation 16 N-(tert-butyl)-1-methylcyclopropane-1-sulfonamide [0104] N-(tert-butyl)-3-chloropropane-1-sulfonamide (Previously dried by azeotroping with 3 x 1OOmL toluene) (100 g, 468 mmol) and THF (1500 niL). This was cooled to an internal temperature of -69 C then butyl lithium (2.5M in hexanes, 412 mL, 1.02 mol) was added dropwise over a period of 55 min while keeping the internal temperature below -65 C. The ice bath was removed and the reaction mixture was warmed to rt over 1.5 h and then cooled back down to an internal temperature of -69 C. Butyl lithium (196 mL, 515 mmol) was added to the reaction mixture over a period of 25 min while keeping the internal temperature below -65 C. The reaction mixture was then warmed to rt over the course of 1.5h. The reaction mixture was recooled to an internal temperature of -69 C and iodo methane (58.5 mL, 936 mmol) was added dropwise over a period of 40 min while keeping the internal temperature below-65 C. The reaction mixture was then warmed to an internal temperature of -50 C over the course of 4h. The cold bath was removed and a solution of saturated NH4C1 (1000 mL) was added. The quenched reaction mixture was transferred to a separatory funnel along with ethyl acetate (100 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. (3 x 75 mL). The combined organic layers were washed with brine (700 mL), dried with MgS04, and concentrated in vacuo to an off white solid which was dried under high vac for 30 min to yield N-(tert-butyl)-1-methylcyclopropane-1 -sulfonamide as a white solid (88.5 g, 99% yield). NMR (500 MHz, CDC13) delta 4.07 (bs, 1 H), 1.51 (s, 3 H), 1.38-1.41 (m, 2 H), 1.36 (s, 9 H), 0.77-0.80 (m, 2 H).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).

81%		A solution of N-tert-Butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyliodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1 H)
81%		A solution of N-tert-Butyl- (3-chloro) propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to-78 C. To this solution was added n- BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to-78C, and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to-78 C over a period of 2 h and a neat solution of methyliodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgS04), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%) :'H NMR (CDCl3) 8 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H)
81%		Step Ib. Preparation ofN-tert-Butyl-(l-methyl)cyclopropylsulfonamide.; A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to - 78 0C. To this solution was added n- BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5h. This mixture was then cooled to - 78C, and a solution of M-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 0C over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated <n="54"/>NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, IH).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).
81%		Step 2: Preparation of N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide A solution of the product of Step 1 (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-butyllithium (17.6 mL, 44 mmol, 2.5M in hexane) slowly. The dry ice bath was removed and the reaction mixture was warmed to room temperature over a period of 1.5 hours. This mixture was cooled to -78 C. and a solution of n-butyllithium (20 mmol, 8 mL, 2.5M in hexane) was added. The reaction mixture was warmed to room temperature, cooled to -78 C. over a period of 2 hours, and treated with a neat solution of methyl iodide (5.68 g, 40 mmol). The reaction mixture was warmed to room temperature overnight, then quenched with saturated NH4Cl (100 mL) at room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil which was crystallized from hexane to provide the desired product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (br s, 1H).
81%		A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to - 78 0C. To this solution was added n- <n="52"/>BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5h. This mixture was then cooled to - 78C, and a solution of M-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 0C over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, IH).
	With n-butyllithium; In tetrahydrofuran; hexane;	(Described above) Steps 2 Preparation of N-tert-Butyl-(1-methyl)cyclopropyl-sulfonamide. A solution of N-tert-Butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to -78 C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to -78 C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to -78 C. over a period of 2 h and a neat solution of methyliodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) delta 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H)

Reference： [1]Patent: US2013/102589,2013,A1 .Location in patent: Paragraph 0072; 0073
[2]Patent: EP2792360,2014,A1 .Location in patent: Paragraph 0104-0105
[3]Synlett,2006,p. 725 - 728
[4]Patent: US2008/107625,2008,A1 .Location in patent: Page/Page column 25
[5]Patent: US2004/77551,2004,A1 .Location in patent: Page/Page column 25
[6]Patent: WO2005/51410,2005,A1 .Location in patent: Page/Page column 81
[7]Patent: WO2008/64061,2008,A1 .Location in patent: Page/Page column 52-53
[8]Patent: US2007/93414,2007,A1 .Location in patent: Page/Page column 40
[9]Patent: US2007/99825,2007,A1 .Location in patent: Page/Page column 29
[10]Patent: US2008/107623,2008,A1 .Location in patent: Page/Page column 24-25
[11]Patent: US2008/107624,2008,A1 .Location in patent: Page/Page column 25
[12]Patent: US2008/119461,2008,A1 .Location in patent: Page/Page column 24
[13]Patent: WO2008/64057,2008,A1 .Location in patent: Page/Page column 50-51
[14]Patent: US2004/48802,2004,A1

14
[ 63132-85-4 ]
[ 140702-33-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.33333 - 2.5h;	A.II.7.C.4 A solution of n-BuLi (74.7 mL, 119.5 mmol, 1.6 M in hexane) was dissolved in dry THF (105 mL) and cooled to -78° C. under a argon atmosphere. To this solution was added a solution of 3-chloropropylsulfonylamine tert-butylcarbamate (14 g, 54.3 mmol) (from Step C.3) in dry THF (105 mL) slowly dropwise over 20-30 minutes. The dry ice bath was removed and the reaction mixture was allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with glacial acetic acid (3.4 mL), concentrated in vacuo, and partitioned between CH2Cl2 (100 mL) and water (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the cyclopropylsulfonylamine tert-butyl carbamate as a waxy off white solid (12.08 g, 100%): 1H NMR (CDCl3) δ 1.10 (m, 2H), 1.34 (m, 2H), 1.50 (s, 9H), 2.88 (m, 1H), 7.43 (s, 1H). 13C NMR (CDCl3) δ 6.21, 28.00, 31.13, 84.07, 149.82.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/10455, 2007, A1 Location in patent: Page/Page column 27

15
[ 63132-85-4 ]
[ 64-18-6 ]
[ 1119798-87-6 ]
3-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}-N-(1,1-dimethylethyl)-1-propanesulfonamide formate salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: N-tert-butyl-(3-chloro)propylsulfonamide; 6-butyl-8-(piperidin-4-yloxy)quinoline With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 6h; Stage #2: formic acid In water; acetonitrile at 20℃; for 0.25h;	34 Example 34 3-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}-N-(1,1-dimethylethyl)-1-propanesulfonamide, dihydrochloride salt To a solution of 6-butyl-8-(4-piperidinyloxy)quinoline (for example, as prepared for Intermediate 4) (0.24 g, 0.84 mmol) in DMF (5 ml) was added sodium iodide (0.22 g, 1.5 mmol), potassium carbonate (0.21 g, 1.5 mmol) and then 3-chloro-N-(1,1-dimethylethyl)-1-propanesulfonamide (for example, as prepared for Intermediate 41) (0.32 g, 1.50 mmol). The slight suspension was heated to 60° C. for 6 h. The mixture was applied to an SCX-2 cartridge (20 g), preconditioned with methanol, and the cartridge washed with methanol (2 column volumes). The cartridge was eluted with 10% 0.880 s.g. ammonia in methanol (2 column volumes) and the basic fractions concentrated in vacuo. The residue (0.36 g) was purified by MDAP and the appropriate fractions combined. The solvent was removed in vacuo to give the formate salt of the title compound (142 mg, 33%): LCMS RT=2.90 min, ES+ve m/z 462 (M+H)+. A portion of the formate salt (47 mg, 0.092 mmol) in methanol (1.5 ml) was treated with 1.25 M hydrogen chloride in methanol (0.5 ml, 0.6 mmol). The solvent was removed using a stream of nitrogen to give the title compound as a yellow solid (49 mg). LCMS RT=2.95 min, ES+ve m/z 462 (M+H)+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/270355, 2009, A1 Location in patent: Page/Page column 43

16
[ 873436-89-6 ]
[ 63132-85-4 ]
[ 1402546-41-1 ]

Yield	Reaction Conditions	Operation in experiment
22%	With caesium carbonate In N,N-dimethyl-formamide at 20℃;	3-(6-Amino-8-((6-iodobenzo[ifl[l,3]dioxol-S-yl)thio)-9jBr-purin-9-yI)-iV-(tert- butyl)propane-l-sulfonamide (WSS3). To a solution of 8-((6-iodobenzo[if)[l,3]dioxol-5- yl)thio-9i/-purin-6-amine (56 mg, 0.13 mmol) in DMF ( 2 mL) was added Af-t-butyl-3- chloro- -propane-l -sulfonamide (144 mg, 0.65 mmol) and Cs2C03 (88 mg, 0.27 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS53 as a white solid (18 mg, 22%). NMR (600 MHz,CDCl3/MeOH-^): δ 8.21 (s, 1H), 7.40 (s, 1H), 7.06 (s, 1H), 6.06 (s, 2H), 4.38 (t, /= 7.3 Hz, 2H), 3.12 (t, J = 7.4 Hz, 2H), 2.13-2.44 (m, 2H), 1.33 (s, 9H); 13C NMR (150 MHz, CDCla/MeOH-rfi): δ 155.8, 153.8, 152.4, 151.5, 151.0, 149.0, 126.7, 121.0, 120.8, 115.3, 104.1, 95.7, 55.7, 51.1, 43.6, 31.5, 25.9; HRMS (ESI) m/z [M+H]+ calcd. forC19H24l 604S2, 591.0345; found 591.0361.

Reference： [1]Current Patent Assignee: MEMORIAL SLOAN-KETTERING CANCER CENTER - WO2012/138894, 2012, A1 Location in patent: Page/Page column 201-202

17
[ 63132-85-4 ]
[ 1119798-87-6 ]
C₂₅H₃₉N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; sodium iodide In N,N-dimethyl-formamide

Reference： [1]Procopiou, Panayiotis A.; Ford, Alison J.; Gore, Paul M.; Hancock, Ashley P.; Hodgson, Simon T.; Holmes, Duncan S.; Looker, Brian E.; Vile, Sadie; Clark, Kenneth L.; Saunders, Ken A.; Slack, Robert J.; Watts, Clarissa J. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4914 - 4919]

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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 63132-85-4 ]

Quality Control of [ 63132-85-4 ]

Related Doc. of [ 63132-85-4 ]

Product Details of [ 63132-85-4 ]

Safety of [ 63132-85-4 ]

Application In Synthesis of [ 63132-85-4 ]

[ 63132-85-4 ] Synthesis Path-Upstream 1~1

[ 63132-85-4 ] Synthesis Path-Downstream 1~17

Related Functional Groups of [ 63132-85-4 ]

Aliphatic Chain Hydrocarbons

Amines

Sulfamides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 63132-85-4 ]