PRODUCTION OF ENDO-HALOPYRIDYL-AZABICYCLOHEPTANE DERIVATIVE AND INTERMEDIATE THEREFOR

PURPOSE:To obtain the subject compound which is a stereoisomer derivative of epibatidine extracted from skin of a toxic frog and having nonopioid analgesic action in high yield by subjecting a compound having a specific structure to deprotection. CONSTITUTION:An endo-halopyridyl-N-protected azabicycloheptane of formula I (R is formyl, allyl, etc.; R is halogen) {e.g. endo-2-(6'-chloro-3'-pyridyl)-7- ethoxycarbonylazabicyc lo-[2.2.1]heptane} is deprotected to provide the objective compound of formula II (X is anion). The protection is preferably carried out by catalytic reduction or acid hydrolysis using hydrochloric acid, etc. Furthermore, the compound of formula I is preferably obtained by successively carrying out reduction, hydrolysis, introduction of N-protecting group, formation of sulfonic acid ester, deprotection and base treatment using a compound of formula III as a starting raw material, introducing a N-protecting group to the produced compound of formula IV, treating the resultant compound with a peracid, etc., and successively reacting the resultant compound of formula V with a halogenating agent.