A Convenient Synthesis of (−)‐Paroxetine | Zendy

Czibula László | Zendy; Nemes András | Zendy; Sebök Ferenc | Zendy; Szántay Csaba | Zendy; Mák Marianna | Zendy

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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)

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