Water → HCID 12961956, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diborane in tetrahydrofurane (257 ml; 1 M) was added dropwise to a stirred solution of 3β,16α-bis(acetyloxy)-5α-androstan-17-one oxime acetate (11.7 g) in tetrahydrofuran (257 ml) at 0° C. under a nitrogen atmosphere. The solution was set aside at room temperature overnight, then water (35 ml) was carefully added to the cooled (0° C.), stirred solution. Tetrahydrofuran was distilled off and replaced with ethanol (400 ml) and sodium hydroxide solution (12 ml; 4 N), and the solution was heated under reflux for 3 h. The solution was concentrated and cooled; water (100 ml) and concentrated hydrochloric acid (12 ml) were added and the solution was heated on a water bath for 1 h. Aqueous sodium hydroxide (2 N) was then added to the cooled solution to precipitate the product, which was filtered off, washed with water and dried in vacuo to give 17β-amino-5α-androstane-3β,16α-diol (6.7 g), m.p. 234°-237° C. (decomp.), [α]D -3.8° (c 1.1 in MeOH).

Provenance & Evidence