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Synthesis of the major metabolites of Paroxetine

AuthorsSegura, Mireia; Roura, Lidia; Torre, Rafael de la; Joglar Tamargo, Jesús
Synthesis of paroxetine metabolites
Issue Date28-May-2003
CitationBioorganic Chemistry 31(3): 284-258 (2003)
AbstractParoxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route.
Description11 pages, 3 figures.-- PMID: 12818234 [PubMed].-- Printed version published Jun 2003.
Publisher version (URL)http://dx.doi.org/10.1016/S0045-2068(03)00040-3
ISSN0045-2068 (Print)
Appears in Collections:(IQAC) Artículos
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