Hydrogen Peroxide → 5-Androstene-3alpha,17beta,19-triol

Participants

Reaction Conditions

Reaction Steps

A 1 M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled in a dry ice-acetone bath to about -78° C. and 17β,19-dihydroxy-5-androsten-3-one in tetrahydrofuran is slowly added. The reaction mixture is stirred for a period of two 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 a 3 N sodium hydroxide solution followed by the addition of a 30% hydrogen peroxide solution. Solid potassium carbonate is added and the tetrahydrofuran solution decanted therefrom. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered, and evaporated. The residue is crystallized from acetone to yield 5-androstene-3α,17β,19-triol.

Provenance & Evidence