(S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol → (S)-2-amino-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

HRID 1845123Notes

Reaction equation

HRID 1845123 reaction equation
[N:1]([C@@H:4]([C:7]1[CH:8]=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[CH2:5][OH:6])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:1][C@@H:4]([C:7]1[CH:8]=[N:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=1)[CH2:5][OH:6]

Participants

4

Reactant 1

HCID 58188243(S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

Product 1

HCID 58188187(S)-2-amino-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-2-azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol (604 mg, 2.60 mmol) in ethyl acetate (28 mL) and 10% Pd—C (70 mg) was stirred under H2 (1 atm) for 1 hr. The catalyst was filtered off and the filtrate was concentrated to afford the title compound. 1H-NMR (300 MHz, CDCl3): 8.64 (s, 1H), 7.86 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=8.1 Hz), 4.16 (m, 1H), 3.73 (dd, 1H, J=10.5, 4.2 Hz), 3.56 (dd, 1H, J=10.4, 7.2 Hz).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a904c0d07ed5413ca2d9836b2a0bc198
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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