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Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C-H Bonds of Drug Molecules.

An efficient deuteration process of beta-amino C-H bonds in various N-alkylamine-based pharmaceutical compounds has been developed. Catalytic reactions begin with the action of Lewis acidic B(C6F5)3 and Brønsted basic N-alkylamine, converting a drug molecule into the corresponding enamine. The acid/base catalysts also promote the dedeuteration of acetone-d6 to afford a deuterated ammonium ion. Ensuing deuteration of the enamine then leads to the formation of beta-deuterated bioactive amines with up to 99% deuterium incorporation.