[ CAS No. 61477-39-2 ]

Name: 61477-39-2|(S)-3-Aminobutan-1-ol|95%
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3d Animation Molecule Structure of 61477-39-2

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Quality Control of [ 61477-39-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 61477-39-2 ]

SDS Specification

Alternatived Products of [ 61477-39-2 ]

Product Details of [ 61477-39-2 ]

CAS No. :	61477-39-2	MDL No. :	MFCD08275763
Formula :	C₄H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AGMZSYQMSHMXLT-BYPYZUCNSA-N
M.W :	89.14 g/mol	Pubchem ID :	9942121
Synonyms :

Calculated chemistry of [ 61477-39-2 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	25.21
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.21
Log Po/w (XLOGP3) :	-0.61
Log Po/w (WLOGP) :	-0.28
Log Po/w (MLOGP) :	-0.18
Log Po/w (SILICOS-IT) :	-0.43
Consensus Log Po/w :	-0.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.12
Solubility :	118.0 mg/ml ; 1.33 mol/l
Class :	Highly soluble
Log S (Ali) :	0.11
Solubility :	115.0 mg/ml ; 1.29 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.09
Solubility :	72.1 mg/ml ; 0.809 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 61477-39-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P301+P330+P331-P302+P352-P304+P340-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 61477-39-2 ]

* 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 [ 61477-39-2 ]
Downstream synthetic route of [ 61477-39-2 ]

[ 61477-39-2 ] Synthesis Path-Upstream 1~7

1
[ 168827-91-6 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(25)-4-hydroxybutan-2- yljcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-l-ol as an oil. 1H NMR (300MHz, OMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] ⁺; measured [a]_D^2a2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]_D²° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2- yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g(92percent) of (3S)-3-aminobutan-1-ol as an oil. ‘H NMR (300MHz, DMSO, ppm): ö 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+Hj measured [cL1D202 +11.650 (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293—2304.).Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-1-ol was isolated as an oil. ‘H NMR (300MHz, DMSO, ppm): ö 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mz, 90 [M+Hj measured [ct1D202 -11.1° (C = 0.32g/lOOmL in EtOH), lit. [ct1D25 -25° (c=1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213—2224.).
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. ¹H NMR (300 MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]⁺; measured [α]_D^20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [α]_D²⁰+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).

92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. ¹H NMR (300 MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]⁺; measured [α]_D^20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [α]_D²⁰+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293 2304.).
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Step 3: (3R)-3-Aminobutan-l-ol and (3y)-3-Aminobutan-l-ol Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4- hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (35)-3-aminobutan-l-ol as an oil. *H NMR (300MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] ⁺; measured [a]_D^{20 2} +11.65° (C=1.22g/100mL in EtOH), lit. [a]_D²⁰ +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293- 2304.). Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-l-ol was isolated as an oil. ^lU NMR (300MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] ⁺; measured [a]_D^{20 2} -11.1° (C = 0.32g/100mL in EtOH), lit. [a]_D²⁵ -25° (c= 1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213-2224).
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) andpalladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. ‘H NMR (300MHz, DMSO, ppm): ö 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS(ESI), mlz, 90 [M+Hj measured [cL1D202 +11.65° (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293—2304.).
92%	With palladium on activated charcoal; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl A^-[(25')-4-hydroxybutan-2- yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3- aminobutan-l-ol as an oil. NMR (300MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] ⁺; measured [a]_D^{20 2} +11.65° (C=1.22g/100mL in EtOH), lit. [a]_D²⁰ +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293-2304.).
92%	With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 12 h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300MHz, DMSO, ppm): δ 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+H] measured [α]_D^20.2°+11.65° (C=1.22g/l00mL in EtOH), lit. [α]_D^20°+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 6], 2293—2304.).

Reference： [1] Patent: WO2014/9447, 2014, A1, . Location in patent: Page/Page column 96; 97
[2] Patent: WO2014/202741, 2014, A1, . Location in patent: Page/Page column 42; 43
[3] Patent: US2015/197529, 2015, A1, . Location in patent: Paragraph 1201; 1204
[4] Patent: US2016/168141, 2016, A1, . Location in patent: Paragraph 1210; 1213
[5] Patent: WO2016/96936, 2016, A1, . Location in patent: Page/Page column 43
[6] Patent: WO2017/5668, 2017, A1, . Location in patent: Page/Page column 40; 41
[7] Patent: WO2017/5900, 2017, A1, . Location in patent: Page/Page column 70
[8] Patent: WO2017/102796, 2017, A1, . Location in patent: Page/Page column 46

2
[ 139243-55-3 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: With sodium hydrogencarbonate In water for 0.25 h; Cooling with ice Stage #2: With potassium borohydride In methanol at 20℃; for 12 h;	(S) -amino-butyric acid methyl ester hydrochloride, 300 mL of methanol and 42 g of potassium borohydride were subjected to a reduction reaction in the same manner as in Example 11 to give 3 (S) -amino-1- Butanol (IV) as a colorless viscous liquid, 27.1 g,Rate of 78percent, ee value of 99.2percent, content of 99.1percent (GC method) 60 g of ethyl 3 (R) -aminobutyrate hydrochloride 63 mL of a 50percent aqueous solution of sodium hydrogencarbonate was carefully added with cooling with ice-water bath. After stirring for 15 minutes, the mixture was extracted three times with dichloromethane (100 mL x 3) , Dried over anhydrous sodium sulfate, filtered and concentrated to dryness (recovered methylene chloride can be applied in the same procedure as described in the next reaction). After adding 300 mL of ethanol to the residue,40 g of potassium borohydride was added in portions at room temperature with stirring, and the reaction was continued at room temperature with stirring,TLC follow the test, about 12 hours of complete reaction, vacuum distillation of ethanol recovery (the next batch reaction in this step the same procedure applied), to the residue by adding 200mL of water, stirring at room temperature with 2N hydrochloric acid carefully adjust PH value to 3- 4, washed three times with dichloromethane (100mL x 3), (combined washing liquid, by distillation of dichloromethane recovery, in the next batch of this step in the same application)The aqueous phase was then adjusted to pH 9 with 2N aqueous sodium carbonate solution, evaporated to dryness under reduced pressure,150 mL of absolute ethanol was added,After thorough stirring, filtration,And then washed with 50mL absolute ethanol filter cake,The organic phases were combined,The ethanol was recovered by distillation at atmospheric pressure (the ethanol fraction was recovered by combining the pre-distillate from the vacuum distillation product,In the next batch of reaction to the same procedure used in this step),Then vacuum distillation,The 59-60 ° C / 10 mm Hg fraction was collected,To give 3 (R) -amino-1-butanol (IV),Colorless viscous liquid, 24.5 g, yield 77percent, ee value 99.2percent, content 99.1percent (GC method)

Reference： [1] Patent: CN105001098, 2016, B, . Location in patent: Paragraph 0099; 0100; 0101; 0102

3
[ 3775-72-2 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran at 20 - 60℃; for 3.5 h;	Add 2 mL of anhydrous tetrahydrofuran and 43 g of anhydrous zinc chloride to the 2L autoclave (with little heat dissipation). Carefully add 24 g of sodium borohydride (note the exotherm and gas production). Stirred at room temperature for 30 minutes and then warmed to 50-60 ° C for 3 hours. After cooling to room temperature, 49 g of the above white solid was added portionwise and the temperature was controlled at 10 to 40 ° C. After the addition was complete, the temperature was slowly raised to reflux for 24 hours. The system became a gray suspension system, cooled to 10-15 ° C, slowly added 25 ml of methanol and 8 g of a 40percent aqueous solution of sodium hydroxide, and the temperature was controlled at 10 to 40 ° C. After adding, stir at room temperature for 3-5 hours. Filtered, washed with THF and filtered to give a colorless liquid. After concentration and distillation under reduced pressure (10 to 65 ° C), 17 g of a clear viscous liquid R-3-aminobutanol was obtained in 47percent yield. Purity 99.1percent, ee99.2percent.

Reference： [1] Patent: CN104370755, 2017, B, . Location in patent: Paragraph 0124; 0126

4
[ 6078-06-4 ]
[ 61477-39-2 ]

Reference： [1] Advanced Synthesis and Catalysis, 2001, vol. 343, # 8, p. 802 - 808

5
[ 61477-38-1 ]
[ 61477-39-2 ]

Reference： [1] The Journal of organic chemistry, 1977, vol. 42, # 9, p. 1650 - 1652

6
[ 5303-65-1 ]
[ 61477-39-2 ]
[ 61477-40-5 ]

Reference： [1] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2895 - 2898

7
[ 5303-65-1 ]
[ 61477-39-2 ]
[ 61477-40-5 ]

Reference： [1] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2895 - 2898

[ 61477-39-2 ] Synthesis Path-Downstream 1~25

1
[ 61477-38-1 ]
[ 61477-39-2 ]

Reference： [1]Journal of Organic Chemistry,1977,vol. 42,p. 1650 - 1652

2
[ 5303-65-1 ]
[ 61477-39-2 ]
[ 61477-40-5 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 2895 - 2898

3
(S)-3-(diphenylmethylamino)butanol [ No CAS ]
[ 101-81-5 ]
[ 61477-39-2 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 2293 - 2304

4
[ 61477-39-2 ]
[ 118715-67-6 ]
C₅₆H₇₂N₆O₁₂ [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1996,vol. 115,p. 357 - 362

5
[ 6078-06-4 ]
[ 61477-39-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2001,vol. 343,p. 802 - 808

6
[ 50-00-0 ]
[ 61477-39-2 ]
[ 1088884-57-4 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7380 - 7395

7
[ 61477-39-2 ]
[ 504-02-9 ]
[ 1246345-01-6 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5887 - 5890
[2]Chemistry - An Asian Journal,2011,vol. 6,p. 573 - 579

8
[ 168827-91-6 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(25)-4-hydroxybutan-2- yljcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-l-ol as an oil. 1H NMR (300MHz, OMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D2a2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2- yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g(92percent) of (3S)-3-aminobutan-1-ol as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+Hj measured [cL1D202 +11.650 (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293?2304.).Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-1-ol was isolated as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mz, 90 [M+Hj measured [ct1D202 -11.1° (C = 0.32g/lOOmL in EtOH), lit. [ct1D25 -25° (c=1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213?2224.).
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300 MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]+; measured [alpha]D20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [alpha]D20+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).

92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300 MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]+; measured [alpha]D20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [alpha]D20+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293 2304.).
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Step 3: (3R)-3-Aminobutan-l-ol and (3y)-3-Aminobutan-l-ol Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4- hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (35)-3-aminobutan-l-ol as an oil. *H NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D20 +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293- 2304.). Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-l-ol was isolated as an oil. lU NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 -11.1° (C = 0.32g/100mL in EtOH), lit. [a]D25 -25° (c= 1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213-2224).
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) andpalladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS(ESI), mlz, 90 [M+Hj measured [cL1D202 +11.65° (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293?2304.).
92%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl A^-[(25')-4-hydroxybutan-2- yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3- aminobutan-l-ol as an oil. NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D20 +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293-2304.).
92%	With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; for 12h;	Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+H] measured [alpha]D20.2° +11.65° (C=1.22g/l00mL in EtOH), lit. [alpha]D20° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 6], 2293?2304.).

Reference： [1]Patent: WO2014/9447,2014,A1 .Location in patent: Page/Page column 96; 97
[2]Patent: WO2014/202741,2014,A1 .Location in patent: Page/Page column 42; 43
[3]Patent: US2015/197529,2015,A1 .Location in patent: Paragraph 1201; 1204
[4]Patent: US2016/168141,2016,A1 .Location in patent: Paragraph 1210; 1213
[5]Patent: WO2016/96936,2016,A1 .Location in patent: Page/Page column 43
[6]Patent: WO2017/5668,2017,A1 .Location in patent: Page/Page column 40; 41
[7]Patent: WO2017/5900,2017,A1 .Location in patent: Page/Page column 70
[8]Patent: WO2017/102796,2017,A1 .Location in patent: Page/Page column 46

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; at 25℃;	General procedure: To a solution of (R)-tert-butyl(4-hydroxybutan-2-yl) carbamate (1.3 g, 6.87 mmol) in methanol (30 mL) was added HC1 (30 mL, 4M in MeOH), stirred at 25°C overnight, concentrated to afford the title compound (0.5 g).

10
[ 61477-39-2 ]
[ 1939-99-7 ]
(3S,6R)-3-methyl-6-phenyl-1,2-thiazinane 1,1-dioxide [ No CAS ]
C₁₁H₁₅NO₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5308 - 5322

11
[ 61477-39-2 ]
[ 4352-30-1 ]
C₁₈H₃₅NO₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;	To a solution of <strong>[61477-39-2](3S)-3-aminobutan-1-ol</strong> (200 mg, 2.24 mmol) and triethylamine (0.79 mL, 5.61 mmol) in tetrahydrofuran (7 mL) at 0 °C was slowly added cyclohexylmethanesulfonyl chloride (1.0 g, 5.16 mmol) and the reaction was stirred at room temperature for 16 hours. Methyl tert-butyl ether (20 mL) was then added to precipitate triethylamine hydrochloride and the salt was removed by filtration. The filtrate was then concentrated to give crude bis-sulfonylated intermediate.

Reference： [1]Patent: WO2015/104353,2015,A1 .Location in patent: Page/Page column 75

12
[ 61477-39-2 ]
[ 124-63-0 ]
C₆H₁₅NO₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;	To a solution of (3S)-3-aminobutan-l-ol (3.0 g, 34 mmol) and triethylamine (12 mL, 84 mmol) in tetrahydrofuran (100 mL) at 0 °C was slowly added methanesulfonyl chloride (6.6 mL, 84 mmol). The reaction was then allowed to worm to room temperature and was stirred at that temperature for 16 hours. Methyl tert-butyl ether (100 mL) was then added to precipitate triethylamine hydrochloride and the salt was removed by filtration. The filtrate was then concentrated to give crude bis-sulfonylated intermediate.

Reference： [1]Patent: WO2015/104353,2015,A1 .Location in patent: Page/Page column 72

13
[ 61477-39-2 ]
[ 1939-99-7 ]
[ 1537863-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;	Prep -N-(4-Chlorobutan-2-yl)- 1 -phenylmethanesulfonamide Step 1 : (R)-3-(Phenylmethylsulfonamido)butyl phenylmethanesulfonate To a solution of (3R)-3-aminobutan-l-ol (1.0 g, 11.2 mmol) and triethylamine (3.3 mL, 23.6 mmol) in tetrahydrofuran (37 mL) at 0 °C was slowly added phenylmethanesulfonyl chloride (4.49 g, 23.6 mmol) and the reaction was stirred at room temperature for 16 hours. MTBE (100 mL) was then added and the Et3N- HC1 salt was removed by filtration. The filtrate was then concentrated to give crude (R)-3-(phenylmethylsulfonamido)butyl phenylmethanesulfonate which was used without purification. LCMS (ESI), m/z, 398 [M+H] +.

Reference： [1]Patent: WO2016/96936,2016,A1 .Location in patent: Page/Page column 43-44

14
[ 61477-39-2 ]
C₁₅H₁₇NO₇ [ No CAS ]
C₁₇H₂₀N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To compound 52 (460 mg, 1.42 mmol) in acetonitrile (20 mL) were added acetic acid (1.0 mL, 17.47 mmol), potassium carbonate (0.8 g, 5.7 mmol) <strong>[61477-39-2](S)-3-aminobutan-1-ol</strong> (0.39 mL, 4.27 mmol). After stirring at 70° C. for 24 h, it was concentrated and the residue was used for the next reaction. The solution of the above residue in THF (20 mL), MeOH (2 mL), and 1 N NaOH (5 mL) was stirred at room temperature for 1 h. The resulting mixture was acidified with 3 N HCl and concentrated to dryness. The residue was purified by column chromatography on silica gel using dichloromethane-20percent methanol in dichloromethane as eluents to get compound 78. LCMS-ESI+ (m/z): [M+H]+ calculated for C17H21N2O6: 349.14. found: 349.15.

Reference： [1]Patent: US2016/289246,2016,A1 .Location in patent: Paragraph 0362; 0363; 0364

15
[ 61477-39-2 ]
[ 4352-30-1 ]
C₁₈H₃₅NO₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 16h;	To a solution of <strong>[61477-39-2](3S)-3-aminobutan-1-ol</strong> (200 mg, 2.24 mmol) and triethylamine (0.79 mL, 5.61 mmol) in tetrahydrofuran (7 mL) at 0° C. was slowly added cyclohexylmethanesulfonyl chloride (1.0 g, 5.16 mmol) and the reaction was stirred at room temperature for 16 hours. Methyl tert-butyl ether (20 mL) was then added to precipitate triethylamine hydrochloride and the salt was removed by filtration. The filtrate was then concentrated to give crude bis-sulfonylated intermediate

Reference： [1]Patent: US2016/311817,2016,A1 .Location in patent: Paragraph 0839; 0840

16
[ 61477-39-2 ]
[ 124-63-0 ]
N-[(1S)-3-chloro-1-methyl-propyl]methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;	To a solution of <strong>[61477-39-2](3S)-3-aminobutan-1-ol</strong> (3.0 g, 34 mmol) and triethylamine (12 mL, 84 mmol) in tetrahydrofuran (100 mL) at 0° C. was slowly added methanesulfonyl chloride (6.6 mL, 84 mmol). The reaction was then allowed to worm to room temperature and was stirred at that temperature for 16 hours. Methyl tert-butyl ether (100 mL) was then added to precipitate triethylamine hydrochloride and the salt was removed by filtration. The filtrate was then concentrated to give crude bis-sulfonylated intermediate.

Reference： [1]Patent: US2016/311817,2016,A1 .Location in patent: Paragraph 0827; 0828

17
3(S)-benzamido-1-butanol [ No CAS ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; for 5h;	Example operating procedures and the same post-processing method implemented by 60g 3 (S) - benzamido-1-butanol, 600mL of concentrated hydrochloric benzoyl hydrolytic reaction to give 3(S)-amino-1-butanol(IV) as colorless viscous liquid, 23.5 g, yield 85percent, ee value 99.3percent, content 99.2percent (GC method), Example 11 Preparation of 3(R)-amino-1-butanol (IV) Take 60g 3 (R) - benzamido-1-butanol, dissolved in 600mL of concentrated hydrochloric acid, into the thick-walled pressure-resistant glass reactor, at 110 deg.] C (external temperature) sealed reactor 5 hours, allowed to stand overnight at room temperature, the precipitated white solid was removed by filtration benzoic acid (37.2g dry weight, recovery rate 99percent, mp.121-122 , 99.5percent can be used benzamide starting material). The aqueous layer was evaporated under reduced pressure, the residue was washed three times with methylene chloride (150mL x 3) with, (washings were combined recoverable by distillation apply). Then, the mixture was carefully added with 55 mL of 50percent sodium hydrogencarbonate aqueous solution under cooling in an ice-water bath, evaporated to dryness under reduced pressure, and 150 mL of absolute ethanol was added thereto. The mixture was stirred well, then filtered and washed with 50 mL of absolute ethanol.The combined filtrate and washings, the first pressure steam to ethanol (ethanol can be applied the next batch) and then vacuum distillation collecting 59-60 / 10mmHg distillate, 3(R)-amino-1-butanol (IV), colorless viscous liquid, 23g, yield 83percent, ee value 99.4percent, content 99.2percent (GC method),

Reference： [1]Patent: CN104961640,2016,B .Location in patent: Paragraph 0088; 0089; 0091; 0092; 0093; 0094; 0095

18
[ 139243-55-3 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
78%		(S) -amino-butyric acid methyl ester hydrochloride, 300 mL of methanol and 42 g of potassium borohydride were subjected to a reduction reaction in the same manner as in Example 11 to give 3 (S) -amino-1- Butanol (IV) as a colorless viscous liquid, 27.1 g,Rate of 78percent, ee value of 99.2percent, content of 99.1percent (GC method) 60 g of ethyl 3 (R) -aminobutyrate hydrochloride 63 mL of a 50percent aqueous solution of sodium hydrogencarbonate was carefully added with cooling with ice-water bath. After stirring for 15 minutes, the mixture was extracted three times with dichloromethane (100 mL x 3) , Dried over anhydrous sodium sulfate, filtered and concentrated to dryness (recovered methylene chloride can be applied in the same procedure as described in the next reaction). After adding 300 mL of ethanol to the residue,40 g of potassium borohydride was added in portions at room temperature with stirring, and the reaction was continued at room temperature with stirring,TLC follow the test, about 12 hours of complete reaction, vacuum distillation of ethanol recovery (the next batch reaction in this step the same procedure applied), to the residue by adding 200mL of water, stirring at room temperature with 2N hydrochloric acid carefully adjust PH value to 3- 4, washed three times with dichloromethane (100mL x 3), (combined washing liquid, by distillation of dichloromethane recovery, in the next batch of this step in the same application)The aqueous phase was then adjusted to pH 9 with 2N aqueous sodium carbonate solution, evaporated to dryness under reduced pressure,150 mL of absolute ethanol was added,After thorough stirring, filtration,And then washed with 50mL absolute ethanol filter cake,The organic phases were combined,The ethanol was recovered by distillation at atmospheric pressure (the ethanol fraction was recovered by combining the pre-distillate from the vacuum distillation product,In the next batch of reaction to the same procedure used in this step),Then vacuum distillation,The 59-60 ° C / 10 mm Hg fraction was collected,To give 3 (R) -amino-1-butanol (IV),Colorless viscous liquid, 24.5 g, yield 77percent, ee value 99.2percent, content 99.1percent (GC method)

Reference： [1]Patent: CN105001098,2016,B .Location in patent: Paragraph 0099; 0100; 0101; 0102

19
[ 3775-72-2 ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium tetrahydroborate; zinc(II) chloride; In tetrahydrofuran; at 20 - 60℃; for 3.5h;	Add 2 mL of anhydrous tetrahydrofuran and 43 g of anhydrous zinc chloride to the 2L autoclave (with little heat dissipation). Carefully add 24 g of sodium borohydride (note the exotherm and gas production). Stirred at room temperature for 30 minutes and then warmed to 50-60 ° C for 3 hours. After cooling to room temperature, 49 g of the above white solid was added portionwise and the temperature was controlled at 10 to 40 ° C. After the addition was complete, the temperature was slowly raised to reflux for 24 hours. The system became a gray suspension system, cooled to 10-15 ° C, slowly added 25 ml of methanol and 8 g of a 40percent aqueous solution of sodium hydroxide, and the temperature was controlled at 10 to 40 ° C. After adding, stir at room temperature for 3-5 hours. Filtered, washed with THF and filtered to give a colorless liquid. After concentration and distillation under reduced pressure (10 to 65 ° C), 17 g of a clear viscous liquid R-3-aminobutanol was obtained in 47percent yield. Purity 99.1percent, ee99.2percent.

Reference： [1]Patent: CN104370755,2017,B .Location in patent: Paragraph 0124; 0126

20
[ 61477-39-2 ]
[ 501-53-1 ]
[ 168827-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water;	The purity was measured directly by gas chromatography. Ee assay: 3-aminobutanol was first reacted with benzyloxycarbonyl chloride in aqueous sodium hydroxide to form N-Cbc-3-aminobutanol and then detected by liquid phase. Column AD-H; Flowable n-hexane: isopropanol (9: 1); flow rate, 1 ml / min. Detection wavelength, 210 nm. Retention time, S-isomer, 11.1 min, R-isomer 12.2 min.

Reference： [1]Patent: CN104370755,2017,B .Location in patent: Paragraph 0124; 0127

21
[ 24424-99-5 ]
[ 61477-39-2 ]
[ 106539-36-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In dichloromethane; at 20℃; for 2h;	[00614] To a solution of Example 127a (10 g, 0.11 mol) and TEA (17 g, 0.17 mol) in DCM (100 mL) was added Boc20 (29.4 g, 0.13 mol), which was stirred for 2 h at room temperature. The reaction mixture was concentrated under reduced pressure and which was purified by silica gel chromatography (Petroleum ether/EtOAc =1/1) to give the desired product Example 127b (11.5 g, yield 55percent) as a white solid.
	In methanol; at 18 - 25℃;	Di-tert-butyl dicarbonate (2.60 mL, 11.22 mmol) was added to a solution of (S)-3- aminobutan-l-ol (1.00 g, 11.2 mmol) in MeOH (10 mL) at room temperature. The mixture was stirred at room temperature and allowed to stand. The mixture was partitioned between water and DCM. The aqueous phase was extracted with DCM. The combined organic phases were dried (MgS04) and concentrated in vacuo. The residue was dissolved in DCM (10 mL), dried (MgS04) and concentrated in vacuo to afford the title compound.H NMR (400 MHz, CD3CN) 5 ppm 1.11 (d, J= 6.69 Hz, 3 H), 1.41 (s, 9 H), 1.44 - 1.51 (m, 1 H), 1.55 - 1.69 (m, 1 H), 2.85 - 3.05 (m, 1 H), 3.43 - 3.58 (m, 2 H), 3.61 - 3.80 (m, 1 H), 5.13 - 5.34 (m, 1 H)
	With triethylamine; In dichloromethane; at 20℃; for 16h;	To a solution of (S)-3-Aminobutan-1-ol (2.00 g, 22.4 mmol) in DCM (10.0 mL) was added TEA (4.74 mL, 33.7 mmol) and di-tert-butyl dicarbonate (5.67 mL, 24.7 mmol). The resulting mixture was stirred at RT for 16 hours. Upon completion, ice water was added, then the aqueous layer was extrated twice with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound (4.12 g, crude).

Reference： [1]Patent: WO2019/51265,2019,A1 .Location in patent: Paragraph 00614
[2]Patent: WO2017/222083,2017,A1 .Location in patent: Page/Page column 50; 51
[3]Patent: WO2019/74962,2019,A1 .Location in patent: Paragraph 0160; 0214

22
(S)-3-amino-1-butanol L-malate [ No CAS ]
[ 61477-39-2 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With potassium ethoxide; In methanol; at 20℃;	27.7g of potassium ethoxide (0.33mol) was added in batches to 200ml of anhydrous methanol, and the temperature was controlled at 10-20°C.After 10 minutes, the system was dissolved, and 36 g of (S)-amino-1-butanol D-malate (0.16 mol) was added and stirred at room temperature for 0.5 to 1 minute.At the time, it is concentrated under reduced pressure (0.1MPa, 30-35°C) to remove most of the methanol, and 40ml of isopropyl acetate is added to continue the concentration and bring out.Residual methanol in the system. Add 200 ml of isopropyl acetate, stir at room temperature for 1 hour, remove the salt with suction, and reduce the amount of isopropyl acetate.Concentrate by pressure (0.1MPa, 40-50°C) to obtain a pale yellow liquid, warm up to 60°C to 90°C to 100°C and distill off at a temperature of 60°C.°C, 12.98 g of a colorless liquid is obtained, namely (S)-3-amino-1-butanol, purity >99percent, chiral purity >99.92percent, yield90.3percent.

Reference： [1]Patent: CN107793320,2018,A .Location in patent: Paragraph 0083; 0084; 0085; 0092; 0093; 0094

23
[ 61477-39-2 ]
C₁₈H₁₇NO₅ [ No CAS ]
C₂₁H₂₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 80℃; for 3h;	(0351) To a solution of Int-2j (1.00 g, 3.06 mmol) in tetrahydrofuran (40 mL) was added acetic acid (0.4 mL) and <strong>[61477-39-2](S)-3-aminobutan-1-ol</strong> (2.72 g, 30.6 mmol). The mixture was stirred at 80° C. for 3 h, cooled to room temperature and purified directly by preparative RP-HPLC to provide Int-10a. 1H NMR (400 MHz, CDCl3) delta 7.57-7.68 (m, 2H), 7.27-7.36 (m, 3H), 6.38-6.47 (m, 1H), 5.30 (d, J=2.8 Hz, 1H), 5.07 (d, J=2.8 Hz, 1H), 4.81-4.98 (m, 1H), 4.27-4.41 (m, 1H), 3.77-4.18 (m, 3H), 2.90-3.11 (m, 2H), 2.35-2.62 (m, 1H), 2.13-2.30 (m, 1H), 1.93-2.10 (m, 2H), 1.19-1.25 (m, 3H); Mass Calc'd for C21H22N2O4: 366.2, found 367.2 (M+H)+.

Reference： [1]Patent: US2018/155365,2018,A1 .Location in patent: Paragraph 0350-0351

24
[ 21240-34-6 ]
[ 61477-39-2 ]
3-[(1S)-3-hydroxy-1-methylpropyl]-4,5-diphenyloxazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		A mixture of (S)-3-Aminobutan-1-ol (4.25 mL, 42.0 mmol) and 4,5-diphenyl-1,3- dioxol-2-one (10.0 g, 42.0 mmol) in DMF (125 mL) was allowed to stir at RT overnight. The reaction was diluted with H2O and extracted with EtOAc (X5), and the combined organic layers washed (H2O X5, brine), dried (Na2SO4) and concentrated in vacuo. The residue was treated with TFA (39.0 mL, 504 mmol) and the solution was allowed to stir for 2 hours. The solution was concentrated and the residue taken up in MeOH and treated with K2CO3(11.9 mL, 210 mmol) and the mixture was allowed to stir for 1 hour. The mixture was concentrated and the residue was diluted with H2O and extracted with EtOAc (X3), and the combined organic layers washed (H2O X2, brine), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (0 to 100percent EtOAc in hexanes) to give a colorless solid (7.60 g, 59percent).

Reference： [1]Patent: WO2019/74962,2019,A1 .Location in patent: Paragraph 0160; 0211

25
[ 61477-39-2 ]
4-chloro-1-methyl-6-nitroquinolin-2(1H)-one [ No CAS ]
4-[[(1S)-3-hydroxy-1-methylpropyl]amino]-1-methyl-6-nitroquinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 20h;Sealed tube; Inert atmosphere;	An oven-dried microwave vial (10-20 ml_ volume) was charged with 4-chloro-1- methyl-6-nitroquinolin-2(1 /-/)-one (Intermediate F1 ; 800 mg, 3.4 mmol) and (S)-3- aminobutan-1-ol (446 mg, 5.0 mmol). The reaction vial was flushed with Ar, sealed with a cap and then further flushed with Ar. Anhydrous NMP (10 ml_) was added followed by DIPEA (1.2 ml_, 6.9 mmol). The reaction mixture was heated at 160C in a heating block for 20 h. The reaction mixture was allowed to cool to rt. The reaction mixture was diluted with water (100 ml_), and the aqueous mixture was extracted with EtOAc (100 ml_). The organic extract was washed with water (2 x 25 ml_). The aqueous washings were combined and further extracted with EtOAc (3 x 50 ml_). The organic extracts were combined, dried (Na2S04) and concentrated in vacuo. The crude reaction mixture was dry-loaded onto silica and purified by flash chromatography (50 g KP-sil; 0% to 10% MeOH in CH2CI2) affording (S)-4-((4- hydroxybutan-2-yl)amino)-1-methyl-6-nitroquinolin-2(1 /-/)-one (547 mg, 56%) as a yellow solid. 1 H NMR (500 MHz, DMSO-cfe) 6 9.1 1 (d, J = 2.5 Hz, 1 H), 8.37 (dd, J = 9.4, 2.5 Hz, 1 H), 7.60 (d, J = 9.4 Hz, 1 H), 7.1 1 (d, J = 7.9 Hz, 1 H), 5.59 (s, 1 H), 4.57 (t, J = 5.0 Hz, 1 H), 3.80-3.71 (m, 1 H), 3.55 (s, 3 H), 3.53-3.48 (m, 2 H), 1.94-1.87 (m, 1 H), 1.67-1.60 (m, 1 H), 1.23 (d, J = 6.4 Hz, 3 H).

Reference： [1]Patent: WO2019/197842,2019,A1 .Location in patent: Paragraph 00284

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
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. 61477-39-2 ]

Quality Control of [ 61477-39-2 ]

Related Doc. of [ 61477-39-2 ]

Product Details of [ 61477-39-2 ]

Calculated chemistry of [ 61477-39-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 61477-39-2 ]

Application In Synthesis of [ 61477-39-2 ]

[ 61477-39-2 ] Synthesis Path-Upstream 1~7

[ 61477-39-2 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 61477-39-2 ]

Aliphatic Chain Hydrocarbons

Alcohols

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 61477-39-2 ]