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A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition

✍ Scribed by Sean R. Donohue; Christer Halldin; Victor W. Pike

Book ID: 104095143
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 107 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.02.132

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✦ Synopsis

Rimonabant is a high-potency cannabinoid type-1 (CB 1 ) receptor inverse agonist that has recently been approved in the European Union as a treatment for obesity. Current methods of synthesis require several steps that have long reaction times and/or lack regioselectivity. Here we present a novel, regioselective synthesis of rimonabant though an enamine-directed 1,3-dipolar cycloaddition. In addition, we present a new and more reactive hydrazonoyl halide for the generation of the requisite nitrile imine dipole.

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