p-Toluenesulfonic acid → 3beta,7alpha-Dihydroxy-5-pregnen-20-one

Participants

Reaction Steps

Reaction of 5α-pregnan-20-one (3) with a mixture of acetic anhydride, acetic acid, and p-toluene sulfonic acid followed by HPLC of the crude product affords the isomeric enol acetates 4 and 5. Epoxidation of 4 and 5 in benzene with m-chloro perbenzoic acid overnight at room temperature furnishes the epoxy acetates 6 and 7. Saponification of both 6 and 7 with methanolic sodium hydroxide gives 17α-hydroxy-5α-pregnan-20-one (8) as a common product.

Provenance & Evidence