Methanol → HCID 12147026, compound

Participants

Reaction Steps

To a solution of 3-(2,2-difluoro-2-phenylethylamino)-1-[(2-ethoxycarbonyl)ethyl]-6-methylpyrazinone (2-11) (0.37 g, 1.01 mmol) in tetrahydrofuran (10 mL) containing 5% methanol, was added sodium borohydride (0.229 g, 6.07 mmol) at room temperature. The reaction mixture was stirred for 5 hours. Then 2 mL of water was added and the mixture was fractionated between dichloromethane and water. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified using a silica gel column chromatography with ethyl acetate/n-hexane (1:1) as eluent to afford the title compound (0.305 g, 93%) as a pale yellow solid. Rf 0.28 (MeOH/CH2Cl2 5/95); 1H-NMR (CDCl3): δ 1.85 (quintet, J=6.4 Hz, 2H), 2.19 (d, J=1.2 Hz, 3H), 3.47 (q, J=6.4 Hz, 2H), 3.65 (t, J=6.8 Hz, 1H), 4.05 (dt, J=6.4, 14.0 Hz, 2H), 4.12 (t, J=6.4 Hz, 2H), 6.14 (t, J=6.4 Hz, 1H), 6.68(d, J=0.8 Hz, 1H), 7.23-7.41 (m, 3H), 7.49-7.52 (m, 2H).

Provenance & Evidence