Catalytic Deuterium Incorporation within Metabolically Stable β-Amino C–H Bonds of Drug Molecules
2019
Chang, Yejin | Yesilcimen, Ahmet | Cao, Min | Zhang, Yuyang | Zhang, Bochao | Chan, Jessica Z. | Wasa, Masayuki
An efficient deuteration process of β-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 β-deuterated bioactive amines with up to 99% deuterium incorporation.
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