The synthesis of a C-labeled C-18 functionalized steroid (as referred as EM-6798) that will serve as a probe for the research of novel antiandrogens has been accomplished. This radioactive steroid was obtained in nine steps by coupling racemic N-cyclohexyl-1-(3'-hydroxy[U- C]phenyl)propylamine with protected 18-bromomethyl-3,17-androstenedione. Incorporation of the radiolabel on the C-18 side chain was achieved using commercially available 3-bromo[U- C]phenol. Alkylation of N-cyclohexyl-1-(3'-hydroxy[U- C]phenyl)propylamine with 3-ethylenedioxy-18-bromomethyl-3,17-androstenedione furnished after reduction and deprotection, [phenyl-U- C]EM-6798 in a 20% overall yield from 3-bromo[U- C]phenol at a specific activity of 156 μCi/mg with 97.9% radiochemical purity as determined by HPLC.
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