Sodium borohydride → HCID 10868268, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 9c (0.037 g 0.16 mmol) in dry tetrahydrofuran (0.5 ml) and dry methanol (0.7 ml), cooled to 0° C. under argon atmosphere, was added in portions sodium borohydride (0.09 g, 0.16 mmol). After stirring for 1 hour at 0° C. the reaction was quenched with a saturated solution of ammonium chloride (1 ml), the solvent was removed and the mixture was extracted with ethyl acetate (3×2 ml). The organic layers were dried and evaporated, the crude product was chromatographed (30% petroleum ether 40-60° in dichloromethane) to give 24c 0.036 g (96% yield). 1H NMR (CDCl3) δ7.40-7.33 (m, 1H); 7.24-7.18 (m, 1H); 6.93-6.84 (m, 2H); 6.33-6.31 (m, 1H); 6.11-6.08 (m, 1H); 5.12-5.04 (m, 1H); 4.91-4.83 (dd, 1H, J=14.22, 2.25 Hz); 4.34-4.24 (dd, 1H, J=14.02, 6.51 Hz); 2.09-2.04 (d, 1H, J=9.83 Hz).

Provenance & Evidence