(S)-3-Aminobutan-1ol Chemical Properties

Boiling point:

168℃

Density 

0.927

Flash point:

56℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Ethanol (Sparingly). Methanol (Slightly)

form 

Oil

pka

15.00±0.10(Predicted)

color 

Colourless to Light Yellow

optical activity

Consistent with structure

Safety Information

RIDADR 

2735

HazardClass 

8

PackingGroup 

Ⅲ

(S)-3-Aminobutan-1ol Usage And Synthesis

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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