Synthesis of the 3-(3,4,5-Trimethoxyphenyl)-pyrrolidine: A New Conformationally Constrained Mescaline Analogue
Synthetic Communications June 1, 2007 Ricardo de L. Barreto, Laura B. L. R. Nascimbem, Carlos Roque D. Correia 8 citations
A new mescaline analogue, 3-(3,4,5-trimethoxyphenyl)-pyrrolidine, was synthesized in four steps from N-Cbz-3-pyrrolidine with a 46% overall yield. The key step was a Heck arylation of a non-activated olefin using a diazonium salt. The resulting hemiaminal intermediate was converted through dehydration with trifluoroacetic anhydride, then hydrogenation and hydrogenolysis, to yield the final compound as a hydrochloride salt. This conformationally constrained analogue may have activity towards 5-HT2 dopamine receptors.