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Type: Artigo de periódico
Title: Synthesis Of The 3-(3,4,5-trimethoxyphenyl)-pyrrolidine: A New Conformationally Constrained Mescaline Analogue
Author: Barreto R.D.L.
Nascimbem L.B.L.R.
Correia C.R.D.
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 N-Cbz-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. Copyright © Taylor & Francis Group, LLC.
Rights: fechado
Identifier DOI: 10.1080/00397910701356504
Date Issue: 2007
Appears in Collections:Unicamp - Artigos e Outros Documentos

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