Sodium borohydride → HCID 69789988, compound

Participants

Reaction Conditions

Reaction Steps

i)—A solution of (3β)-3-(acetyloxy)androsta-5,14-dien-17-one [Andre, A. F. St. et al, J. Am. Chem. Soc. 74, 5506 (1952); 42.9 g] in dry ethanol (429 ml) was cooled to −10° C. Sodium borohydride (1.51 g) in dry ethanol (33.5 ml) was added and the mixture was stirred at −10° C. for 7.5 h. Excess sodium borohydride was destroyed by careful addition of an aqueous solution of acetic acid (50%). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated. Column chromatography provided (3β,17β)-androsta-5,14-diene-3,17-diol 3-acetate (19.5 g).

Provenance & Evidence