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CAS No. : | 61477-39-2 | MDL No. : | MFCD08275763 |
Formula : | C4H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AGMZSYQMSHMXLT-BYPYZUCNSA-N |
M.W : | 89.14 | Pubchem ID : | 9942121 |
Synonyms : |
|
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: |
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* 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.
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.). |
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). |
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. |
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. |
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] +. |
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. |
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 |
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. |
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), |
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) |
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