A Convenient Synthesis of (−)-Paroxetine

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)...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-08, Vol.2004 (15), p.3336-3339
Main Authors: Czibula, László, Nemes, András, Sebök, Ferenc, Szántay Jr, Csaba, Mák, Marianna
Format: Article
Language:English
Subjects:
Antidepressants
Azabicycloheptane intermediates
Hydrogenation
Neighboring-group effects
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400067