Cyclohexanone → HCID 70479340, compound

Participants

Reaction Steps

Sodium cyanoborohydride (2.0 g) and cyclohexanone (2.0 ml) were added to a solution of Intermediate 2 (2.0 g) in ethanol (30 ml) and the mixture was stirred for 24 h. The mixture was diluted with NaHCO3 solution and extracted with ethyl acetate (3×). The extract was washed with water, dried and evaporated to give a solid. This was dissolved in ethyl acetate and extracted with dilute hydrochloric acid (3×) and water (2×). These extracts were brought to pH 10 with 0.88 NH3 solution and then extracted with ethyl acetate (3×). The ethyl acetate extract was washed with water, dried and evaporated to give a solid. This was purified by crystallisation from ethyl acetate to give the title compound (1.67 g), m.p. 199°-202°, [α]D +6.5°.

Provenance & Evidence