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A chiral synthesis of dapoxetine hydrochloride, a serotonin reuptake inhibitor, and its 14C isotopomer

✍ Scribed by William J. Wheeler; Douglas D. O'bannon

Publisher: John Wiley and Sons
Year: 1992
Tongue: French
Weight: 472 KB
Volume: 31
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580310406

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✦ Synopsis

Abstract

The ^14^C‐isotopomer of dapoxetine‐[^14^C] HCl (S (+)‐N,N‐dimethyl‐α‐[2‐(1‐naphthalenyloxy)ethyl‐2‐^14^C]benzenemethanamine hydrochloride, 1a), a potent serotonin re‐uptake inhibitor has been prepared by a chiral synthesis, starting with tert.‐butyloxyphenylglycine (3). Borane reduction, followed by activation of the resulting alcohol 4 as its mesylate 5b, provided the chiral starting material. The radiolabel was introduced by reaction of 5b with sodium cyanide‐[^14^C]. The desired product (1) was then elaborated from nitrile 6a,b via a five step synthesis in an overall 19.5% radiochemical yield.

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