Identification | Back Directory | [Name]
(S)-3-Aminobutan-1ol | [CAS]
61477-39-2 | [Synonyms]
(S)-3-Aminobutan-1ol (S)-3-Amin-1-butanol (3S)-3-aminobutan-1-ol (3S)-3-Amino-1-butanol (+)-(S)-3-aMinopropan-1-ol 1-Butanol, 3-amino-, (3S)- 1-Fmoc-4-(Cbz-amino)piperidine-4-carboxylic acid | [Molecular Formula]
C4H11NO | [MDL Number]
MFCD08275763 | [MOL File]
61477-39-2.mol | [Molecular Weight]
89.14 |
Chemical Properties | Back Directory | [Boiling point ]
168℃ | [density ]
0.927 | [Fp ]
56℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Ethanol (Sparingly). Methanol (Slightly) | [form ]
Oil | [pka]
15.00±0.10(Predicted) | [color ]
Colourless to Light Yellow | [Optical Rotation]
Consistent with structure |
Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
(S)-3-Aminobutan-1-ol can be used as an intermediate in the preparation of compounds having HIV integrase inhibitory activity. | [Synthesis]
General procedure for the synthesis of (S)-3-aminobutanol from (S)-benzyl(4-hydroxybutan-2-yl)carbamate: To a 1000 mL round bottom flask was added a solution of (S)-benzyl(4-hydroxybutan-2-yl)carbamate (30 g, 134.4 mmol, 1.00 eq.) in methanol (500 mL), followed by the addition of palladium carbon (3 g, 0.10 equivalent). The reaction mixture was stirred at 25 °C for 12 h under hydrogen atmosphere. Upon completion of the reaction, the solid catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 11.7 g (92% yield) of (S)-3-aminobutan-1-ol as a colorless oil. The product was confirmed by 1H NMR (300 MHz, DMSO-d6, 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); the LCMS (ESI) analysis showed a m/z of 90 [M + H]+; the specific spectroscopy measurement value of [α]D22 +11.65° (c = 1.22 g/100 mL in EtOH) is consistent with the literature value of [α]D20 +16.3° (c = 4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304). | [References]
[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 |
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