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A Convenient Synthesis of (−)‐Paroxetine
Author(s) -
Czibula László,
Nemes András,
Sebök Ferenc,
Szántay Csaba,
Mák Marianna
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400067
Subject(s) - chemistry , piperidine , stereocenter , mesylate , methanol , stereoselectivity , paroxetine , hydrogenolysis , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , receptor , serotonin
A convenient synthesis of the antidepressant paroxetine starting from 1‐benzyl‐4‐piperidone ( 2 ) is reported. A stereoselective reduction resulted in cis ‐piperidine‐3‐methanol [( + )‐ 6 ]. The reaction between cis ‐piperidine‐3‐methanol mesylate ( 7 ) and sesamol led to benzyl‐protected trans ‐paroxetine ( 9 ) through an inversion reaction of the stereogenic center at position 3. The latter compound was deprotected by hydrogenolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)