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).
O'Donnell
Christopher J
CJ
Pfizer Global Research and Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA. christopher_j_odonnell@groton.pfizer.com
Singer
Robert A
RA
Brubaker
Jason D
JD
McKinley
Jason D
JD
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