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Paper | Regular issue | Vol 98, No. 2, 2019, pp.215-223
Published online, 22nd January, 2019
DOI: 10.3987/COM-18-14016
Efficient Synthesis of Chiral 5-Methoxycarbonylpyridin-2(1H)-ones and 3-Bromo-5-methoxycarbonylpyridin-2(1H)-ones

Hugo Pilotzi, Dino Gnecco,* María L. Orea,* David M. Aparicio, Sylvain Bernes, Jorge R. Juárez, and Joel L. Terán

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC9 Complejo de Ciencias, C.U., 72570 Puebla, Mexico

Abstract

Starting from the mixture methyl-(S)-3-(1-phenylethylamino)acrylate 1-(E,Z) and the mixture methyl (R)-3-(2-(tert-butyldimethylsilyl)oxy-1-phenylethyl)amino acrylate 2-(E,Z) were synthesized the corresponding chiral 5-carbomethoxy-pyridin-2(1H)-ones in high yield. Finally, starting from these chiral pyridin-2(1H)-ones were prepared the corresponding 3-bromo-5-carbomethoxy-pyridin-2(1H)-ones in high yield.