Synthesis of optically pure epibatidine analogs: (1R, 2R, 5S)-2β-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane and (1R, 2S, 5S)-2α-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane from (-)-cocaine

Article abstract of DOI:10.1016/S0040-4039(97)01276-8

Two optically pure epibatidine analogs, 4 and 5, which contain the 8-azabicyclo[3.2.1]octane ring system were synthesized from (-)-cocaine. The nicotinic receptor binding affinity and the stimulant activity of 4 and 5 were measured to be significantly lower than racemic epibatidine (±-1).