Sodium borohydride → t-Butyl {2-[4-(3-hydroxy-propenyl)-benzoylamino]-phenyl}-carbamate

Participants

Reaction Steps

To a stirred solution of compound XVI (1.00 g, 2.79 mmol) in ethanol (15 ml) under nitrogen was added sodium borohydride (110 mg, 2.73 mmol). After 5 min, the reaction mixture was quenched with water and diluted with AcOEt. After separation the organic layer was successively washed with brine, dried over MgSO4, filtered, and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60) to afford the title compound XVIII (910 mg, 2.29 mmol, 82% yield) as a pale yellow solid (slightly contaminated with the diene). 1H NMR (300 MHz, CDCl3) δ(ppm): 9.20 (s, 1H), 7.90 (d, J=7.8 Hz, 2H), 7.75 (d, J=7.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.32–7.08 (m, 3H), 6.94 (s, 1H), 6.65 (d, J=15.9 Hz, 1H), 6.45 (td, J=15.9, 5.4 Hz, 1H), 4.35 (d, J=5.4 Hz, 2H), 1.92 (s, 1H), 1.51 (s, 9H).

Provenance & Evidence