Sodium borohydride → (3-(4-(4-Chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol

Participants

Reaction Steps

To a solution of 1-(3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol (Preparation 27C, 0.05 g, 0.118 mmol) in methanol (1.0 mL) at 0° C. was added a solution of sodium periodate (0.030 g, 0.142 mmol) in water (1.0 mL) dropwise. The white heterogeneous reaction mixture was stirred for 40 mins. at the same temperature and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhyd. sodium sulfate and concentrated. The residue was taken in methanol (2 mL) and treated with sodium borohydride (5.35 mg, 0.142 mmol) at room temperature. After 1 h, the reaction was quenched with saturated. aq. sodium bicarbonate. After stirring for 30 min, the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over anhyd. magnesium sulfate and concentrated to yield (3-(4-(4-chlorophenyl)cyclohexyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)methanol.

Provenance & Evidence