1beta-Methyl-5alpha-androstane-3beta,17beta,19-triol 3,17-diacetate → 3beta,17beta-Dihydroxy-1beta-methyl-5alpha-androstan-19-one diacetate

Participants

Reaction Conditions

Reaction Steps

One equivalent of Jones reagent is added dropwise to a stirred solution of 1β-methyl-5α-androstane-3β,17β,19-triol 3,17-diacetate in acetone chilled to 0° C. After 15 minutes at 0° C., the acetone layer is poured onto ice water. The solid which forms is filtered and crystallized from an ether-hexane solution to yield 3β,17β-dihydroxy-1β-methyl-5α-androstan-19-one diacetate. This material is dissolved in aqueous methanol containing sodium carbonate and the solution heated at its reflux temperature for about 4 hours. The cooled solution is poured onto water and filtered. The solid which forms is collected and is crystallized from an ether-hexane solution to yield 3β,17β-dihydroxy-1β-methyl-5α-androstan-19-one.

Provenance & Evidence