Merck + Co., Inc.

Joann M Um

Nobuyoshi Yasuda

Barry M Trost

David Alan Conlon

Michael Palucki

Processes are disclosed for preparing 3-hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists. A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo&lsqb;3.1.0&rsqb;hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu&equals;the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo&lsqb;3.1.0&rsqb;hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.

Growing community of inventors

Franklin Lakes, NJ, United States of America

Joann M Um