An improved synthesis of enantiomerically pure RWJ 69442, a development candidate for the treatment of benign prostatic hyperplasia

✍ Scribed by Gee-Hong Kuo; Catherine Prouty; William V. Murray; Rekha D. Shah

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2001
• Tongue: English
• Weight: 39 KB
• Volume: 38
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570380433

✦ Synopsis

Abstract

This report describes an improved synthesis of enantiomerically pure (S)‐2‐[4‐(Dimethylamino)phenyl]‐2,3‐dihydro‐N‐[2‐hydroxy‐3‐[4‐[2‐(1‐methylethoxy)‐phenyl]‐1‐piperazinyl]propyl]‐1,3‐dioxo‐1__H__‐isoindole‐5‐carboxamide (RWJ 69442), a potent and selective α~la~‐adrenergic receptor antagonist for the treatment of benign prostatic hyperplasia. The synthesis highlights less hazardous reagents, easier purification and higher enantiomeric purity. The N‐benzyl‐N—t‐butoxycarbonyl amine 6 could serve as an enantiomerically pure chiral building block for asymmetric synthesis.