N-methyl-2,5-di(trimethyl silyl) pyrrolidine → (1R,2R,4S)-2-(6-Chloropyridin-3-yl)-7-methyl-7-azabicyclo[2.2.1]heptane

Participants

Reaction Steps

To a acetonitrile solution containing 3 gms of Ag (1)F. 1.2 gms of dipolarophile (6-chloro-3-vinyl pyridine) was added to 2 gms of N-methyl-2,5-di(trimethyl silyl) pyrrolidine at 25° C. After stirring the reaction mixture for 2 to 2.5 hours, the reaction mixture was filtered through a plug of celite. The solvent was evaporated to give N-methyl Epibatidine in 80% yield which was further purified by column chromatography. Hydrogenation of N-methyl Epibatidine with pd/c for 22 hours gave 70% yield of Epibatidine.

Provenance & Evidence