Cyclohexanone → HCID 12804706, compound

Participants

Reaction Steps

A solution of 11α-amino-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one 20-ethylene acetal (2 g) in ethanol (20 ml) was stirred with cyclohexanone (1.5 ml) and sodium cyanoborohydride (2.015 g) for 6 h. 5% NaHCO3 solution (40 ml) was added and the mixture was extracted with ether (x2). The extract was washed with water (x2), dried and evaporated to leave a froth which was dissolved in 2M-HCl solution (50 ml) and ethanol (50 ml). Water (100 ml) was added and the mixture was washed with ether (x2). The wash was extracted with 2M-HCl solution and the combined acid fraction was brought to basic pH with 2M-NaOH solution. The mixture was extracted with ether (x2) and the extract was washed with water (x2), dried and evaporated to leave a froth which was purified by column chromatography eluted with CHCl3 :MeOH (9:1) to give the title compound (1.235 g), [α]D +39°. νmax 1695 cm-1.

Provenance & Evidence