John Hutchinson

Nitrogen bridge homoepibatidines. syn-6- and syn-5(6-chloro-3-pyridyl)isoquinuclidines

Abstract The N-bridge vicinal-6(6-Cl-3-pyridyl) and distal 6-(6-Cl-3-pyridyl)-2-azabicyclo[2.2.2]octane homologs of the potent nicotinic receptor agonist epibatidine have been synthesized. Key steps involve stereo-selective catalytic hydrogenations of both 6- and 5-(6-Cl-3-pyridyl)-2-azabicyclo[2.2.2]oct-5-enes 12 and 17 on the face anti to the nitrogen containing bridges. The vicinal homolog appears to be a potent nicotinic agonist.