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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 : |
|
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 Ų |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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 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]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 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]D20.2+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]D20.2+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]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): 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]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 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]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 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]D20.2° +11.65° (C=1.22g/l00mL in EtOH), lit. [α]D20° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 6], 2293—2304.). |
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) |
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. |
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