N-(1-(3,5-difluoropyridin-2-yl)vinyl)acetamide → (S)-N-(1-(3,5-Difluoropyridin-2-yl)ethyl)acetamide

HRID 75947Notes

Reaction equation

HRID 75947 reaction equation
[F:1][C:2]1[C:3]([C:9]([NH:11][C:12](=[O:14])[CH3:13])=[CH2:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1>CO>[F:1][C:2]1[C:3]([C@@H:9]([NH:11][C:12](=[O:14])[CH3:13])[CH3:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 1

HCID 66736036N-(1-(3,5-difluoropyridin-2-yl)vinyl)acetamide

Product 1

HCID 66735495(S)-N-(1-(3,5-Difluoropyridin-2-yl)ethyl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(1-(3,5-difluoropyridin-2-yl)vinyl)acetamide (Method 53, 2.2 g, 11.1 mmol) in MeOH (20 ml) under N2 was added (+)-1,2-bis((2S,5S)-2,5-dimethyl phospholano)benzene (cyclooctadiene)rhodium(I)trifluoromethanesulfonate (0.074 g, 0.111 mmol). The solution was transferred to a high-pressure bomb and charged 150 psi H2. The reaction stirred at room temperature and maintained inside pressure between 120-150 psi for 24 hours. The solvent was removed and the resulted residue was purified by column chromatography (EtOAc) to give the title compound as a white solid (2.0 g, 90%). 1H NMR (400 MHz) δ 8.47 (d, J=2.4 Hz, 1H), 8.34 (d, J=7.2 Hz, 1H), 7.89 (m, 1H), 5.21 (m, 1H), 1.81 (s, 3H), 1.34 (d, J=6.8 Hz, 3H). MS: Calcd.: 200. Found: [M+H]+ 201.

Workup

  1. additioncharged 150 psi H2
  2. temperaturemaintained inside pressure between 120-150 psi for 24 hours
  3. customThe solvent was removed
  4. customthe resulted residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-4b16d4b0d88441ac8580208cf2b7c62f
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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