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61477-39-2

61477-39-2 Structure

61477-39-2 Structure
IdentificationBack 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 PropertiesBack 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
[InChI]

1S/C4H11NO/c1-4(5)2-3-6/h4,6H,2-3,5H2,1H3/t4-/m0/s1
[InChIKey]

AGMZSYQMSHMXLT-BYPYZUCNSA-N
[SMILES]

C[C@H](N)CCO
Hazard InformationBack 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]

benzyl (S)-(4-hydroxybutan-2-yl)carbamate

168827-91-6

(S)-3-Aminobutan-1ol

61477-39-2

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
Safety DataBack Directory
[RIDADR ]

2735
[WGK Germany ]

WGK 3
[HazardClass ]

8
[PackingGroup ]

[Storage Class]

11 - Combustible Solids
Spectrum DetailBack Directory
[Spectrum Detail]

(S)-3-Aminobutan-1ol(61477-39-2)1HNMR
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