Efficient and practical synthesis of enantiomerically pure spirobenzazepine derivative

ORGN 524

H. Marlon Zhong1, Arnold Braier2, Penina Feibush1, John Hortenstine1, Birdella Kenney1, Cynthia Maryanoff1, Roland Müller2, Max Rey2, Martin Rettig2, Lorraine Scott1, and Frank Villani1. (1) Drug Evaluation, Chemical and Pharmaceutical Development, Johnson & Johnson Pharmaceutical Research and Development, L.L.C, Welsh and McKean Roads, Spring House, PA 19477, (2) Laboratory for Process Research, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
The substituted spirobenzazepine derivative 1 is a nonpeptide mixed V1a/V2 vasopressin receptor antagonist that is developed for treatment and/or prevention of conditions involving increased vascular resistance and cardiac insufficiency. The process used for the large-scale preparation of the synthetically challenging spirobenzazepine key intermediate 2 as a single enantiomer will be described in this presentation.

 

Practical Synthesis and Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004