Photoredox Deuteration in flow

The effects of deuteration at specific positions on drug molecules has been an area of interest for many years, with links between H-D substitution and improved pharmacokinetic properties, decreased metabolism, and reduced toxicity and
epimerisation being made since the 1960s.1 However, the first deuterated drug, deutetrabenazine, was only approved by the FDA in 2017. Additionally, deuterated molecules have been utilised as reference compounds in ADME studies. The
application of deuteration techniques in the process of deuterated drug production is still being developed. Existing methods utilise forcing conditions, or use of expensive pressurised D2 gas.2
In 2017, MacMillan et al. presented
photoredox-catalysed methodology for deuteration of α-amino carbon atoms in APIs using D2O.3 The use of flow chemistry has been shown to be a viable means for scale up of other photochemical reactions,4,5 and we herein present our
attempts to investigate the effects of transferring MacMillan’s chemistry to a flow paradigm.

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