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A chiral synthesis of dapoxetine hydrochloride, a serotonin reuptake inhibitor, and its 14 C isotopomer
Author(s) -
Wheeler William J.,
O'ban Douglas D.
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580310406
Subject(s) - chemistry , serotonin reuptake inhibitor , nitrile , hydrochloride , chemical synthesis , stereochemistry , serotonin , organic chemistry , biochemistry , in vitro , receptor
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.