Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

S W Gerritz; J S Smith; S S Nanthakumar; D E Uehling; J E Cobb

doi:10.1021/ol0067641

Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines

Org Lett. 2000 Dec 14;2(25):4099-102. doi: 10.1021/ol0067641.

Authors

S W Gerritz¹, J S Smith, S S Nanthakumar, D E Uehling, J E Cobb

Affiliation

¹ Glaxo Wellcome, Inc., Five Moore Drive, P.O. Box 13398, Research Triangle Park, North Carolina 27709, USA. swg25518@glaxowellcome.com

PMID: 11112653
DOI: 10.1021/ol0067641

Abstract

[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol. In all cases studied, the cis-1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepine was obtained as the major product.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzazepines / chemical synthesis*
Cyclization
Dopamine Antagonists / chemical synthesis*
GTP-Binding Proteins / metabolism
Indicators and Reagents
Receptors, Dopamine D1 / antagonists & inhibitors

Substances

Benzazepines
Dopamine Antagonists
Indicators and Reagents
Receptors, Dopamine D1
GTP-Binding Proteins