A general route to the synthesis of 1,5-methano- and 1,5-ethano- 2,3,4,5-tetrahydro-1H-3-benzazepines.
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).
Pfizer Global Research and Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA. christopher_j_odonnell@groton.pfizer.com
Christopher J
CJ
O'Donnell
Robert A
RA
Singer
Jason D
JD
Brubaker
Jason D
JD
McKinley
D001552:Benzazepines / Q000138:chemical synthesis*; D002384:Catalysis; D007189:Indans / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry
D001552:Benzazepines; D007189:Indans; D007202:Indicators and Reagents; D009570:Nitriles; C430593:cyanohydrin