Direct reductive alkylation of amine hydrochlorides with aldehyde bisulfite adducts

M Barniol-Xicota, AL Turcu, S Codony, C Escolano…

Index: Barniol-Xicota, Marta; Turcu, Andreea L.; Codony, Sandra; Escolano, Carmen; Vazquez, Santiago Tetrahedron Letters, 2014 , vol. 55, # 15 p. 2548 - 2550

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Abstract

Surprisingly, the direct use of the bisulfite adducts of aldehydes in reductive amination reactions has scarcely been reported in the scientific literature. In a pioneering work, Pandit and Mani reported in 2009 that secondary amines may be reductively alkylated with aldehyde bisulfite adducts using NaBH(OAc) 3 in anhydrous 1,2-dichloroethane at room temperature. 9 The expected tertiary amines were isolated in high yields (>80%). Two drawbacks of this method are that it was ...