Hydrogen Peroxide → HCID 70628079, compound

Participants

Reaction Conditions

Reaction Steps

A 1 M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled in a dry iceacetone bath to about -78° C. and 19-hydroxyandrost-4-ene-3,17-dione acetate in tetrahydrofuran is slowly added. The reaction mixture is stirred for a period of 2 hours at this temperature, warmed to 0° C., and stirring continued for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide followed by the addition of a 30% hydrogen peroxide solution. Care is taken that the solution temperature remains below 10° C. during decomposition. Solid potassium carbonate is added and the tetrahydrofuran decanted. The solid residue is washed with tetrahydrofuran and the combined solutions are dried over sodium sulfate, filtered and evaporated. The residue which remains is crystallized from acetone to yield 4-androstene-3α,17β,19-triol 19-acetate.

Provenance & Evidence