Synthesis of Amino Compounds under Phase Transfer Conditions

Abstract

Abstract The phase transfer process was applied to the reaction of organic bromides with azide anion. The reduction of intermediary azide derivatives gave the corresponding amino compounds, benzylamine, glycine, alanine, butyrine, and serine in fairly good yields. Effective catalytic activity was demonstrated by the difference in chemical yields in the case of methyl bromoacetate and ethyl α-bromopropionate. In order to examine the role of phase transfer catalyst, two bromohydrins (methyl β-hydroxy-α-bromopropionate and styrene bromohydrin) were subjected to the present reaction. Methyl β-hydroxy-α-bromopropionate afforded serine exclusively in the presence of 18-crown-6 and tetrabutylammonium bromide, but in the absence of the catalyst a mixture of serine and isoserine was obtained. A different regioselectivity was observed in the case of styrene bromohydrin.