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Synthesis 2023; 55(05): 821-825
DOI: 10.1055/a-1972-3819
DOI: 10.1055/a-1972-3819
paper
One-Step, Gram-Scale Synthesis of Caffeine-d 9 from Xanthine and CD3I
Authors
We would like to acknowledge the Natural Sciences and Engineering Research Council (NSERC) of Canada for funding through the Alliance Grant program (Grant ALLRP 566659-21).
Dedicated to Andrew T. B. Stuart, P.Eng., in recognition of his contributions to clean hydrogen and deuterium technologies.
Abstract
A one-step, gram-scale synthesis of caffeine-d 9 was achieved using xanthine and CD3I. The reaction proceeds at room temperature using dimsyl sodium as base and THF as solvent, and conducting the reaction on a 1-g scale gave caffeine and caffeine-d 9 in 77% and 86% yield, respectively, after recrystallization.
Publication History
Received: 07 September 2022
Accepted after revision: 04 November 2022
Accepted Manuscript online:
04 November 2022
Article published online:
29 November 2022
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Given that theobromine (3) and theophylline (5) are naturally occurring desmethylcaffeine alkaloids also isolable from the hulls of cacao beans or tea, these have commonly served as synthetic precursors to caffeine, see: