Asymmetric synthesis of (R)-(+)-[[(2-bromoethyl)amino]methyl]-2-nitro-1H-imidazole-[1-14C]-ethanol monohydrobromide

The enantioselective synthesis of (R)-(+)-2-(tert-butyldiphenylsiloxylmethyl)[C-14]oxirane from C-14-labeled barium carbonate was accomplished This labeled oxirane facilitated an asymmetric synthesis (R)-(+)-[[(2-bromoethyl)amino]methyl]-2-nitro-1H-imidazole-[1-C-14]-ethanol monohydrobromide (CI-1010), a potent hypoxic cell selective radiosensizing anti-cancer agent. From labeled barium carbonate the labeled oxirane was prepared in 26.2% yield, and this gave the target labeled CI-1010 in 17% yield.