Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/79265
Type: Artigo de periódico
Title: Synthesis of the 3-(3,4,5-trimethoxyphenyl)pyrrolidine: A new conformationally constrained mescaline analogue
Author: Barreto, RD
Nascimbem, LBLR
Correia, CRD
Abstract: The total synthesis of the 3-(3,4,5-trimethoxyphenyl)-pyrrolidine, a new and conformationally constrained mescaline analogue, was accomplished in a concise and efficient manner. The synthetic route encompassed only 4 steps from the starting NCbz-3- pyrrolidine, in 46% overall yield. The route features a highly effective Heck arylation of the non-activated olefin N-Cbz-3-pyrrolidine with the 3,4,5-trimethoxybenzene diazonium tetrafluoroborate. The hemiaminal (lactamol) Heck adduct was converted to the mescaline analogue in a sequence of reactions: ( a) dehydration of the intermediate hemiaminal 3 with trifluoroacetic acid anhydride, (b) hydrogenation/ hydrogenolysis of the endocyclic enecarbamate 6 with H2-Pd/C, and (c) formation of the rather stable mescaline analogue in the form of a hydrochloride salt. The target molecule constitutes a new mescaline analogue with potential activity towards 5-HT2 dopamine receptors.
Subject: arenediazonium tetrafluoroborates
3-aryl pyrrolidines
heck arylation
mescaline analogues
Country: EUA
Editor: Taylor & Francis Inc
Rights: fechado
Identifier DOI: 10.1080/00397910701356504
Date Issue: 2007
Appears in Collections:Unicamp - Artigos e Outros Documentos

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