A Convenient Synthesis of (−)-Paroxetine

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)...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2004-08, Vol.2004 (15), p.3336-3339
Hauptverfasser: Czibula, László, Nemes, András, Sebök, Ferenc, Szántay Jr, Csaba, Mák, Marianna
Format: Artikel
Sprache:eng
Schlagworte:
Antidepressants
Azabicycloheptane intermediates
Hydrogenation
Neighboring-group effects
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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