A facile synthesis of deuterium labeled 2,2-dimethyl-[~2H_6]-succinic acid and its anhydride

摘要

Deuterium labeled 2,2-dimethyl-[~2H_6]-succinic anhydride by a sequence of reactions involving Knoevenagel condensation of [~2H_6]-acetone with ethyl cyanoacetate in the presence of piperidine, Michael addition of cyanide, HCI hydrolysis, simultaneous decarboxylation, and subsequent dehydration using acetic anhydride in an overall yield of 34.23% based on [~2H_6]-acetone utilized in the reaction is reported. The title compounds were characterized and confirmed spectroscopically by Fourier transform infrared, ~1H-NMR, and Mass. The chemical purity as determined by HPLC was 99%. To the best of our knowledge, the synthesis of these specifically deuterium labeled compounds has not been reported so far.