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

Abstract

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.