Enantioselective synthesis of a 2,2-disubstituted tetrahydro-3-benzazepine as Novel NMDA receptor antagonist

3Citations
Citations of this article
7Readers
Mendeley users who have this article in their library.

Abstract

The tricyclic oxazolidines trans-4 and cis-4 were interconverted upon treatment with allyltrimethylsilane/TiCl4. The oxazolidine trans-4 was diastereoselectively reacted with PhMgBr to yield the 4,4-disubstituted 3-benzazepinone 6, along with two side products. An X-ray crystal structure analysis of 6 proved the (R)-configuration of the stereogenic center C-4 and thus the retention of configuration. Reduction of 6 with AlCl 3/LiAlH4 (1/3) followed by hydrogenolysis with H 2, Pd/C resulted in the formation of enantiomerically pure 2-methyl-2-phenyl-tetrahydro-3-benzazepine 11 which has a moderate affinity (Ki = 496 nM) to the PCP binding site of the NMDA receptor. © 2010 Verlag der Zeitschrift für Naturforschung, Tübingen.

Cite

CITATION STYLE

APA

Husain, S. M., Fröhlich, R., Schepmann, D., & Wünsch, B. (2010). Enantioselective synthesis of a 2,2-disubstituted tetrahydro-3-benzazepine as Novel NMDA receptor antagonist. Zeitschrift Fur Naturforschung - Section B Journal of Chemical Sciences, 65(2), 191–196. https://doi.org/10.1515/znb-2010-0216

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free