The synthesis of 6‐chloro‐17‐hydroxypregna‐4,6‐diene‐3,20‐dione‐4−14c acetate (chlormadinone‐4−14C acetate)

Chlormadinone-4−14C acetate (V) was synthesized from 17α-hydroxyprogesterone-4−14C (I) by dehydrogenation to the 4,6-diene (II) which was converted to the 6-chloro-4,6-diene (IV) via the intermediate 6α,7α-epoxy compound (III). Acetylation of (IV) gave chlormadinone-4−14C acetate in 13% overall yield. A secondary reaction product, 6-chloro-androsta-4,6-diene-3,17-dione-4−14C was isolated and identified.