[ CAS No. 13374-31-7 ] {[proInfo.proName]}

Name: 13374-31-7|(1R,2R)-2-Aminocyclohexanol hydrochloride|97%
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SKU: A320048
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Quality Control of [ 13374-31-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 13374-31-7 ]

CAS No. :	13374-31-7	MDL No. :	MFCD09259962
Formula :	C₆H₁₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LKKCSUHCVGCGFA-KGZKBUQUSA-N
M.W :	151.63	Pubchem ID :	12228412
Synonyms :

Safety of [ 13374-31-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13374-31-7 ]

* 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.

Downstream synthetic route of [ 13374-31-7 ]

[ 13374-31-7 ] Synthesis Path-Downstream 1~58

1
[ 155975-19-2 ]
[ 13374-31-7 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5631 - 5634

2
[ 1012792-56-1 ]
[ 13374-31-7 ]
[ 1012792-57-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 72h;	c) 6-Chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide; 6-Chloro-5-(4-chloro-phenyl)-nicotinic acid (1.4 g, 5 mmol) was dissolved in N,N-dimethylformamide (30 mL). To this solution was added sequentially (1R,2R)-2-amino-cyclohexanol hydrochloride (0.87 g, 6 mmol), TBTU (1.84 g, 6 mmol), and N-ethyldiisopropylamine (4.47 mL, 26 mmol). The reaction mixture was stirred at room temperature for 72 hours then concentrated in vacuo. The residue was then dissolved in ethyl acetate (100 mL) and washed with 0.5 N HCl (100 mL), saturated sodium bicarbonate (100 mL) and water (100 mL). The aqueous phases were extracted with ethyl acetate (2×100 mL), the organics were combined and the whole was dried over MgSO4 and concentrated in vacuo. The solid residue was purified by stirring with (ethylacetate/heptane 1:2, 50 mL) to give 6-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide as a colorless solid, 1.4 g (73% yield). m/z (ISP+): 364.9, 366.9 (M+H).

Reference： [1]Patent: US2008/70931,2008,A1 .Location in patent: Page/Page column 11
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 9874 - 9896

3
6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinic acid [ No CAS ]
[ 13374-31-7 ]
N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 20h;	g) N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide; A solution of (1R,2R)-2-amino-cyclohexanol hydrochloride (41 mg, 0.27 mmol) in N,N-dimethylformamide (1.2 ml) was added to a suspension of TBTU (234 mg, 0.73 mmol), 6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinic acid (0.24 mmol) and N-ethyldiisopropylamine (0.21 ml, 1.22 mmol) in N,N-dimethylformamide (1.7 ml). The reaction mixture was shaken at room temperature for 20 hours then concentrated in vacuo. The residue was then dissolved in dichloromethane (2 ml) and washed with water (2 ml). The aqueous layer was separated and extracted with dichloromethane (2 ml), the organics were combined and the whole was dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative HPLC to afford N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide, 49 mg (44% yield over 2 steps). LC at 215 nm; Rt 3.92: 92%, m/z (ES+): 471 (M+H).

Reference： [1]Patent: US2008/70931,2008,A1 .Location in patent: Page/Page column 13

4
[ 953771-16-9 ]
[ 13374-31-7 ]
tert-butyl 4-(2-((1R,2R)-2 hydroxycyclohexylamino)-benzo[d]thiazol-6-yloxy)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 72h;	Step 3. Preparation of tert-butyl 4-(2-((1R,2R)-2 hydroxycyclohexylamino)-benzo[d]thiazol-6-yloxy)picolinate To the solution of tert-butyl 4-(2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)picolinate (500 mg, 1.25 mmol) in 10 ml of NMP was added (1R,2R)-cyclohexane-1,2-diamine (581 mg, 3.84 mmol) and DIPEA (0.995 ml, 5.76 mmol). The reaction solution was stirred at 100 C. for 3 days. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give tert-butyl 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinate (240 mg, 0.544 mmol) as white powder. ES/MS m/z 442.5 (MH+).

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 80-81

5
[ 2605-14-3 ]
[ 13374-31-7 ]
[ 953771-25-0 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. Preparation of (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol To the solution of 2-chloro-6-methoxybenzo[d]thiazole (1.0 g, 5 mmol) in 5.5 ml of NMP was added <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (910 mg, 6 mmol) and DIPEA (2.44 ml, 14 mmol). The reaction solution was stirred at 115 C. for 96 hours. The crude reaction solution was purified by prep HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with ethyl acetate (2*300 ml). The combined organic layers were washed with water (60 ml) and brine (60 ml), then dried over Na2SO4 and evaporated in vacuo to give (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) as an ivory solid. ES/MS m/z 279.1 (MH+).
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 115℃; for 96h;	NMP was added (IR, 2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong> (910 mg, 6 mmol) and DIPEA (2.44 mL, 14 mmol). The reaction solution was stirred at 1 15 C for 96 hours. The crude reaction solution was purified by preparative HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with EtOAc (2x 300 mL). The combined organic layers were washed with water (60 mL) and brine (60 mL), then dried over Na2SO4 and evaporated in vacuo to give (lR,2R)-2-(6- methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) as an ivory solid. ES/MS m/z 279.1(MH+).

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 82
[2]Patent: WO2008/144062,2008,A1 .Location in patent: Page/Page column 83

6
[ 911056-05-8 ]
[ 13374-31-7 ]
[ 953771-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20 - 125℃; for 12h;	Step 2. Synthesis of (1R,2R)-2-(7-bromo-6-methoxybenzo[d]thiazol-2ylamino)cyclohexanol To the solution of 7-bromo-2-chloro-6-methoxybenzo[d]thiazole (150 mg, 0.539 mmol, 1.0 eq) in 1 mL of NMP was added <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (0.123 mg, 0.809 mmol, 1.5 eq) and DIPEA (263 muL, 1.503 mmol, 2.8 eq) at room temperature. The reaction mixture was stirred at 125 C. for 12 hours, thereafter the mixture was diluted with saturated sodium bicarbonate solution (ca. 100 mL) and aqueous layer extracted with ethyl acetate (ca. 200 mL*3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give crude product as brown oil which was sufficiently pure and was carried to next step without further purification. LC/MS (m/z) [359.0] (MH+)

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 96

7
[ 953771-80-7 ]
[ 13374-31-7 ]
4-(7-chloro-2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 0.25h;Microwave;	Step 4. Synthesis of 4-(7-chloro-2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide To the solution of 4-(7-chloro-2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)-Nmethylpicolinamide (10 mg, 0.026 mmol, 1.0 eq) in NMP was added <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (6 mg, 0.039 mmol, 1.5 eq) and DIPEA (13 muL, 0.078 mmol, 3.0 eq) and reaction mixture heated at 160 C. in microwave for 15 min. Thereafter, the product was purified via reverse phase HPLC. LC/MS (m/z) [433.1] (MH+)

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 98

8
[ 953770-72-4 ]
[ 13374-31-7 ]
4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]oxazol-6-yloxy)-N-methylpicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20℃; for 48h;	Example 201 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]oxazol-6-yloxy)-N-methylpicolinamide To the solution of N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide (25 mg, 0.075 mmol, 1.0 eq) in 1 mL of NMP was added <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (17 mg, 0.112 mmol, 1.5 eq) and DIPEA (40 muL, 0.225 mmol, 3.0 eq) and reaction mixture stirred at room temperature for 48 hours. Thereafter, the product was purified via reverse phase HPLC. LC/MS (m/z) [383.1] (MH+)

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 100

9
(1R,2R)-1-amino-2-benzyloxycyclohexane [ No CAS ]
[ 13374-31-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In 1,4-dioxane; methanol; at 0℃;	Synthesis of (1R,2R)-2-aminocyclohexanol hydrochloride To an ice bath cooled solution of amine (1R,2R)-(-)-2-Benzyloxycyclohexylamine (20 g, 97.4 mmol) in dry MeOH (390 mL) was added 4.0 M HCl solution in dioxane (49 mL, 195 mmol) slowly via syringe. The ice bath was removed and resulting solution was sparged with N2 for 10 min. 10% Pd/C (3 g, 28 mmol) was added to the solution and the reaction was purged with H2 and maintained under a H2 atmosphere. After 4 h, an additional 10 mL of 4.0 M HCl solution in dioxane was added2 and the reaction was maintained under a H2 atmosphere overnight. Upon completion (followed by LCMS), the reaction was filtered through a thin, tightly packed pad of Celite and the collected solids were washed successively with MeOH and EtOAc. The combined organic filtrates were evaporated and dried under vacuum gave (1R,2R)-2-aminocyclohexanol hydrochloride as a pale-colored solid, (13.8 g, 91 mmol, 93%). LCMS m/z 116.0 (MH+), tR=0.37 min.
93%		To an ice bath cooled solution of amine (lR,2R)-(-)-2-benzyloxycyclohexylamine (20 g, 97.4 mmol) in dry MeOH (390 mL) was added 4.0 M HCl solution in dioxane (49 mL, 195 mmol) slowly via syringe. The ice bath was removed and resulting solution was sparged with N2 for 10 min. 10 % Pd/C (3 g, 28 mmol) was added to the solution and the reaction was purged with H2 and maintained under a H2 atmosphere. After 4 h, an additional 10 mL of 4.0 M HCl solution in dioxane was added and the reaction was maintained under a H2 atmosphere overnight. Upon completion (followed by LCMS), the reaction was filtered through a thin, tightly packed pad of Celite and the collected solids were washed successively with MeOH and EtOAc. The combined organic filtrates were concentrated under reduced pressure to provide (lR,2R)-2-aminocyclohexanol hydrochloride as a pale-colored solid, (13.8 g, 91 mmol, 93 %). LCMS m/z 116.0 (MH+), Rt = 0.37 min.

Reference： [1]Patent: US2008/45528,2008,A1 .Location in patent: Page/Page column 101
[2]Patent: WO2008/144062,2008,A1 .Location in patent: Page/Page column 82-83

10
[ 1018782-86-9 ]
[ 13374-31-7 ]
6-(2-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃; for 72h;	To a solution of 0.10 g 6-(2-chloro-phenyl)-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid in 3.0 ml of DMF is added at room temperature 0.082 g 1,1'-carbonyl-diimidazole, 0.22 ml N-ethyldiisopropylamine and 0.057 g (1R,2R)-2-amino-cyclohexanol hydrochloride and stirred for 72 hours. To the mixture is added citric acid 10% solution and ethyl acetate. The organic layer is washed with sodium bicarbonate 10% solution and sodium chloride saturated solution. The organic layer is separated and dried over sodium sulfate and evaporated at the rotary evaporator. The residue is purified by chromatography on silica gel with heptane/ethyl acetate 40/60 to yield 0.055 g of the title compound as white solid, MS (ISP) 401.3 (M+H)+.

Reference： [1]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 30-31

11
[ 108-24-7 ]
[ 13374-31-7 ]
[ 214348-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; acetone; at 0 - 20℃;	(1R,2R)-2-Amino-cyclohexanole hydrochloric acid (25.0 g, 164.9 mmol) was dissolved in acetone (160 ml). To this solution was added at 0 C. with stirring aqueous sodium carbonate (163.7 ml, 169.8 mmol) and within 10 minutes acetic anhydride. The reaction mixture was stirred at room temperature for 2 h and the solvent evaporated. The residue was treated at room temperature with ethanol (200 ml), stirred for 5 min. After filtration the solvent was evaporated and treated with dichloromethane (300 ml), stirred at reflux for 2 h and again filtered. The solvent of the filtrate was evaporated to yield the title compound (25.9 g) as white solid; MS (ISP) 158.2 (M+H)+.

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 11151 - 11160
[2]Patent: US2009/247588,2009,A1 .Location in patent: Page/Page column 11

12
[ 105-36-2 ]
[ 13374-31-7 ]
ethyl [(trans-2-aminocyclohexyl)oxy]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.5%		To a solution of trans-2-amino-cyclohexanol hydrochloride (455 mg, 3.0 mmol) in THF (7 mL) was added sodium hydride (78 mg, 3.25 mmol) under argon. The mixture was stirred at rt for 12 h before ethyl bromoacetate (500 mg, 3.0 mmol) was added, and the solution was stirred at rt for another 12 h. After filtration, the solution was concentrated and the residue taken up in CH2C12 and washed with brine. The organic layer was separated and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate) to afford the desired product (51 mg, 8.5% yield) : LC-MS m/z 202.2 (MH+), retention time 0.73 min (method 1); Rf = 0.23 (ethyl acetate).

Reference： [1]Patent: WO2005/99705,2005,A2 .Location in patent: Page/Page column 52

13
[ 1236405-08-5 ]
[ 13374-31-7 ]
[ 1236404-48-0 ]

Yield	Reaction Conditions	Operation in experiment
6%		Example 46 N-[3-([(1R,2R)-2-hydroxycyclohexyl]amino}methyl)-8-methylquinolin-7-yl]-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide [Show Image] N-(3-Formyl-8-methylquinolin-7-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide (1.0 g) obtained in Reference Example 9 and <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (1.52 g) were suspended in 1-methyl-2-pyrrolidone (20 mL) and acetic acid (7.0 mL) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (2.35 g) was added and the mixture was stirred at room temperature for 3 hr. 1N Aqueous sodium hydroxide solution was added to quench the reaction and basify the mixture. The mixture was partitioned and extracted with ethyl acetate, the organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL), and the mixture was washed with ethyl acetate. 1N Aqueous sodium hydroxide solution was added to the aqueous layer, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was recrystallized from ethyl acetate-diisopropyl ether to give the title compound (78 mg, yield 6%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) delta: 0.98 - 1.17 (6 H, m), 1.59 - 2.00 (8 H, m), 2.26 (1 H, br), 2.64 (3 H, s), 3.16 - 3.19 (1 H, m), 3.68 - 3.73 (1 H, m), 3.77 - 3.91 (2 H, m), 4.00 - 4.05 (2 H, m), 4.17 - 4.19 (1 H, m), 4.64 - 4.67 (1 H, m), 7.08 (2 H, d, J=8.7 Hz), 7.57 (1 H, d, J=8.7 Hz), 7.78 (1 H, d, J=8.7 Hz), 8.01 (2 H, d, J=8.7 Hz), 8.21 (1 H, s), 8.90 (1 H, s), 10.05 (1 H, s). melting point: 142-143C elemental analysis value (C29H35N3O4·0.6H2O) Calculated: C, 69.60; H, 7.29; N, 8.40. Found: C, 69.30; H, 7.09; N, 8.16.

Reference： [1]Patent: EP2392573,2011,A1 .Location in patent: Page/Page column 69

14
5-(3,4-dichlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinoyl chloride [ No CAS ]
[ 13374-31-7 ]
[ 1269826-44-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		A solution of (lR,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong> (298.0 g, 1.97 mol) in a mixture of THF (2.4 1) and water (2.4 1) was treated at room temperature with NaOH (759.0 ml, 8.19 mmol) and stirred for 1 h. The biphasic mixture was heated to ca. 38C, treated at this temperature within 45 min with the above described acid chloride and stirred for 45 min at ca. 38C. After addition of ethanol (2.19 1) and stirring for 5 min, water (4.8 1) was added. The mixture was heated to 60C and the organic solvent exchanged with ethanol (9.6 1) under reduced pressure keeping the total volume constant. The formed suspension was stirred for 3 h at room temperature, filtered and the crystals washed with a mixture of ethanol (2.1 1) and water 2.1 1) followed by water (3.0 1). After drying the product was isolated in 95%. MS(TurboSpray): 465 (M+H+, 70%), 463 (M+H+, 100%).
	With sodium hydroxide; In tetrahydrofuran; water; at 38℃; for 1.5h;	Example 85-(3,4-Dichloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamideTo a solution of 5-(3,4-dichloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (600 g, 1.64 mmol) in a mixture of THF (3.6 l) and DMF (4.0 ml) was added at room temperature within 1 h oxalyl chloride (215.0 ml, 2.46 mol). The reaction mixture was stirred for 1 h at room temperature (acid chloride formation).A solution of <strong>[13374-31-7](1R,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong></strong> (298.0 g, 1.97 mol) in a mixture of THF (2.4 l) and water (2.4 l) was treated at room temperature with NaOH (759.0 ml, 8.19 mmol) and stirred for 1 h. The biphasic mixture was heated to ca. 38 C., treated at this temperature within 45 min with the above described acid chloride and stirred for 45 min at ca. 38 C. After addition of ethanol (2.19 l) and stirring for 5 min, water (4.8 l) was added. The mixture was heated to 60 C. and the organic solvent exchanged with ethanol (9.6 l) under reduced pressure keeping the total volume constant. The formed suspension was stirred for 3 h at room temperature, filtered and the crystals washed with a mixture of ethanol (2.1 l) and water 2.1 l) followed by water (3.0 l). After drying the product was isolated in 95% yield. MS (TurboSpray): 465 (M+H+, 70%), 463 (M+H+, 100%).

Reference： [1]Patent: WO2012/52444,2012,A1 .Location in patent: Page/Page column 16
[2]Patent: US2012/101282,2012,A1 .Location in patent: Page/Page column 8

15
[ 13374-31-7 ]
(5aR,9aR)-3-bromo-2-phenyl-5-tosyldecahydrobenzo[b][1,4]oxazepine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

16
[ 13374-31-7 ]
[ 1421070-78-1 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

17
[ 13374-31-7 ]
N-cinnamyl-N-((1R,2R)-2-hydroxycyclohexyl)-4-nitrobenzenesulfonamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

18
[ 13374-31-7 ]
N-cinnamyl-N-((1R,2R)-2-hydroxycyclohexyl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

19
[ 98-59-9 ]
[ 13374-31-7 ]
[ 245085-44-3 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

20
[ 13374-31-7 ]
[ 98-74-8 ]
C₁₂H₁₈N₂O₅S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 872 - 885

21
[ 931-15-7 ]
[ 13374-31-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2895 - 2897

22
[ 70-34-8 ]
[ 13374-31-7 ]
[ 26344-04-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2895 - 2897

23
[ 286-20-4 ]
[ 13374-31-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2895 - 2897
[2]Organic Letters,2013,vol. 15,p. 2895 - 2897

24
[ 1194973-45-9 ]
[ 13374-31-7 ]
[ 1439905-63-1 ]

Yield	Reaction Conditions	Operation in experiment
330 mg		4-(3-(2H-l,2,3-Triazol-2-yl)phenylamino)-2-(methylthio)pyrimidine-5-carboxamide (300 mg, 0.91 mmol) was dissolved in 15 mL NMP. To it was added MCPBA (77%, 340 mg, 1.38 mmol). The mixture was stirred for 40 m at RT. To it were added DIEA (1.58 mL, 9.1 mmol) and (lR,2R)-<strong>[13374-31-7]2-aminocyclohexanol hydrochloride</strong> (415 mg, 2.73 mmol). The mixture was stirred at 90C for 2.5 h. It was cooled to RT, diluted with 300 mL EtOAc, washed with IN NaOH and brine, dried, concentrated in vacuo, and subjected to reverse phase preaparative HPLC to isolate the title compound (330 mg). MS found for C19H22N802 as (M+H)+ 395.3. UV: lambda=254 nm.

Reference： [1]Patent: WO2013/78468,2013,A1 .Location in patent: Paragraph 0321; 0322

25
[ 13374-31-7 ]
[ 110716-78-4 ]

Yield	Reaction Conditions	Operation in experiment
280 mg	With dmap; sodium azide; trifluoromethylsulfonic anhydride; In dichloromethane; at 20℃;	Sodium azide (2.43 g, 18.7 mmol) was dissolved in 7.6 mL water and stirred in ice bath. To it were added 8 mL DCM and then Tf20 (1.28 mL, 7.6 mmol).The mixture was stirred for 2 h in ice bath. The DCM phase was separated, and the aqueous phase was extracted with DCM twice. The combined DCM phase was washed with sat. NaHC03 and water, dried over MgS04. (lR,2R)-2-Aminocyclohexanol hydrochloride (302 mg, 2.0 mmol) was dissolved in 5 mL dry DCM and stirred at RT. To it were added DMAP (1.07 g, 8.8 mmol) and then the above- prepared TfN3/DCM solution dropwise. The mixture was stirred for overnight. It was concentrated in vacuo and subjected to flash column to isolate (1R,2R)-2-azidocyclohexanol (280 mg, a clear oil). Proton NMR: (CDC13) delta 3.34 (1H, m), 3.14 (1H, m), 2.87 (1H, s), 1.99 (2H, m), 1.69 (2H, m), 1.31-1.18 (4H, m) ppm.

Reference： [1]Patent: WO2013/78468,2013,A1 .Location in patent: Paragraph 0326; 0327

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