N-(1-(5-Fluoropyridin-2-yl)vinyl)acetamide → (S)-N-(1-(5-Fluoropyridin-2-yl)ethyl)acetamide

Participants

Reaction Steps

To a solution of N-(1-(5-fluoropyridin-2-yl)vinyl)acetamide (Intermediate 2, 11.0 g, 61.1 mmol) in MeOH (120 ml) under N2 was added (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I)trifluoromethanesulfonate (0.441 g, 0.611 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 7 hours. The solvent was removed and the resulted residue was purified by column chromatography (EtOAc) to give the title compound as a white solid (9.8 g, 88%). 1H NMR (400 MHz) δ 8.49 (d, J=2.4 Hz, 1H), 8.32 (d, J=7.6 Hz, 1H), 7.66 (m, 1H), 7.39 (dd, J=4.4 and 8.8 Hz, 1H), 4.95 (m, 1H), 1.85 (s, 3H), 1.34 (d, J=7.2 Hz, 3H). MS: Calculated: 182. Found: [M+H]+ 183. Enantiomeric excess determined by HPLC (Chiralpak IA; 70:30 CO2/MeOH), 95.3% ee.

Provenance & Evidence