The decarboxylation of amino acids is an important synthetic route to biologically active amines. Enzymatic decarboxylation of amino acids occurs in many organisms and has long been reported as a synthetic option for the decarboxylation of the amino acid L-Histidine. Microwave-promoted rapid decarboxylation of L-Histidine and other L-amino acids via stable imine formation with R-Carvone is herein described.Acidic hydrolysis of the imines at elevated temperatures forms amine hydrochloride salts in greater than 99% purity with isolable product yields ranging from 60-90% overall. This synthetic transformation is well-suited for the undergraduate laboratory due to the overall simplicity of the decarboxylation and the exceptionally clean product yields for naturally occurring L-amino acids.

Microwave assisted decarboxylation of L-histidine and other amino acids via imine formation with R-carvone

247th National Meeting (2014)

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