Base-catalyzed Reaction of β-Halo-α-Alanine Methyl Ester

Abstract

The reaction of 8-halo-a-alanine methyl ester hydrohalide (halogen=Cl, Br) in the presence of organic or inorganic base catalysts was studied.
As a result, unexpected a, a'-dicarbomethoxy divinylamine [6] was obtained in 50, -75% yield and neither 2, 5-dicarbomethoxy piperazine C 2 nor other expected compounds C3 D 5 were isolated.
The structure of C 6 was determined by IR, 'H-NMR, C-NMR and Mass spectra. Hydrogenation of C 6D gave a, a'-dicarbomethoxy diethylamine [11], 1 which was identified by IR and 'H-NMR spectra.