Synthesis of [2H]5-epitestosterone

Isotopically pure d 5 -epitestosterone has been synthesized for the first time. This polydeuterated 17α-hydroxyandrosterone was prepared by H/D exchange reaction with MeOD-D 2 O under basic conditions. Its characteristics are described in detail, including its enolization into a d 4 -heterodienic silyl ether derivative upon silylation