Preparation of 1,5-methano-2,3,4,5- tetrahydro-1H-3-benzazepine via Pd-catalyzed cyclization.

Org Lett

Chemical Research and Development, Pfizer Global Research and Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA.

Published: July 2004

[reaction: see text] A new approach to prepare 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzanepine (1) is discussed. This strategy utilized a tandem Michael addition and Pd-catalyzed cyclization to afford cyanobenzofulvene acetal 13. This indene intermediate (13) was subjected to hydrogenolysis to provide an amino ester (12) and was cyclized with base to afford lactam 5. The lactam (5) was reduced with borane to afford the desired benzazepine (1).

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http://dx.doi.org/10.1021/ol049316sDOI Listing

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