(S)-3-Oxiranyl-pyridine → (R)-2-amino-1-(pyridin-3-yl)ethanol

Reaction equation

[O:1]1[CH2:3][C@H:2]1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.CO.[NH4+:12]>>[NH2:12][CH2:3][C@@H:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[OH:1]

Participants

Reactant 2

HCID 13319559(S)-3-Oxiranyl-pyridine

HCID 22220579Ammonium methanol

Product 1

HCID 23556080(R)-2-amino-1-(pyridin-3-yl)ethanol

Procedure

The title compound was prepared from 3-[(2R)-oxiranyl]pyridine (which was obtained in Example 134) and saturated ammonium methanol in substantially the same manner, as described in Example 124. The product was obtained as a brown oil; 1H NMR (300 MHz, DMSO-d6) δ 1.70 (brs, 2H), 2.62-2.74 (m, 2H), 4.46-4.50 (m, 1H), 5.20 (brs, 1H), 7.30-7.34 (m, 1H), 7.68-7.71 (m, 1H), 8.42-8.50 (m, 2H); MS (ES) m/z: 139 (MH+).

Workup

customThe product was obtained as a brown oil

Sources & evidence

ORD record: ord-ebc4da04f4104abc9dab65d4b83f802b
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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