O'Donnell Christopher J, Singer Robert A, Brubaker Jason D, McKinley Jason D
Pfizer Global Research and Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA.
J Org Chem. 2004 Aug 20;69(17):5756-9. doi: 10.1021/jo049122q.
A general approach to preparing 1,5-methano- (1) and 1,5-ethano-2,3,4,5-tetrahydro-1H-3-benzazepine (2) is discussed. This strategy involves converting an indanone or tetralone (4) to a cyanohydrin (3) which is subjected to hydrogenolysis followed by lactamization and reduction to provide bicyclic aryl piperidine (1) and bicyclic aryl homopiperidine (2).