PRODUCTION OF HALOPYRIDYL-AZABICYCLOHEPTANE DERIVATIVE AND INTERMEDIATE THEREFOR

PURPOSE:To obtain the subject compound useful as a nonopioid-based analgesic agent by deprotecting a halopyridyl-N-protected azabicycloheptane derivative. CONSTITUTION:A sulfonyl-N-protected azabicycloheptene derivative expressed by formula I (R is formyl a lower aliphatic acyl, vinyl, lower alkoxycarbonyl, etc.; R is methyl, ethyl, phenyl or toluyl) is reacted with sodium amalgam to provide an N-protected azabicycloheptene derivative expressed by formula II, which is then reacted with a halogenated pyridine in the presence of a palladic salt to afford a pyridyl-N-protected azabicycloheptane derivative expressed by formula III. The resultant compound is subsequently oxidized with aqueous hydrogen peroxide, a peracid or an organic peroxide to provide an N-oxyhalopyridyl-N-protected azabicycloheptane derivative expressed by formula IV, which is further reacted with a halogenating agent to afford a halopyridyl-N-protected azabicycloheptane derivative expressed by formula V (R is halogen). The obtained compound is subsequently deprotected to provide the objective compound expressed by formula VI (X is anion).