Synthesis of β-Dimethylaminoethyl and α-Hydroxy-β-Dimethylaminoethyl Derivatives from Organolithium Compounds and Tetramethyoxamide

Abstract

Abstract The important biological activity of a variety of aromatic and heterocyclic systems having β-dimethylaminoethyl side chains and their α-hydroxy analogs (c.f. bufotenin, N-methylepinephrine, etc.) has focused the attention of the organic chemist on methods of introducing these functions, and a variety of approaches have been developed. A convenient synthesis has recently been reported3, which utilizes the α-hydroxy-β-dimethylaminoethyl function as an intermediate in the preparation of β-dimethylaminoethyl derivatives, thus providing either or both of these pharmacophoric groups.