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An efficient synthesis of S ‐γ‐[(4‐trifluoromethyl)‐phenoxy]benzenepropanamine‐[1‐ 14 C] maleate, an important metabolite of fluoxetine hydrochloride
Author(s) -
Wheeler William J.
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.2580310207
Subject(s) - chemistry , trifluoromethyl , hydrochloride , borane , metabolite , medicinal chemistry , diol , ether , stereochemistry , organic chemistry , catalysis , biochemistry , alkyl
S ‐γ‐[(4‐Trifluoromethyl)phenoxy]benzenepropanamine‐[1‐ 14 C] maleate has been prepared in six steps from R ‐(‐)1‐phenyl‐1,2‐ethanediol. The isotope was incorporated by the reaction of NaCN‐[ 14 C] with the tert. butyldimethylsilyl ether of R ‐(‐)1‐phenyl‐1,2‐ethane‐diol 2‐tosylate. Borane reduction and arylation, followed by salt formation yielded S ‐γ‐[(4‐trifluoromethyl)phenoxy]benzenepropanamine‐[1‐ 14 C] maleate.