Synthesis of 5-(Hydroxymethyl)pyrrolidin-2-ones by Cyclization of Amide Dianions with Epibromohydrin

Ilia Freifeld, Holger Armbrust, Peter Langer*

*Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Email: peter.langeruni-rostock.de

I. Freifeld, H. Armbrust, P. Langer, Synthesis, 2006, 1807-1808.

DOI: 10.1055/s-2006-942354

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Abstract

The reaction of amide and thioamide dianions with epibromohydrin resulted in regioselective formation of 5-(hydroxy­methyl)pyrrolidin-2-ones (pyroglutaminols) and -thiones.

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proposed reaction pathway

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Key Words

lactams, cyclizations, dianions, epoxides, heterocycles, regio­selectivity

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ID: J66-Y2006-1590