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A Convenient Synthesis of (−)-Paroxetine

✍ Scribed by László Czibula; András Nemes; Ferenc Sebök; Csaba Szántay Jr.; Marianna Mák

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
111 KB
Volume
2004
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

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)

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