Organic process research and development p. 588 - 598 (2020)
Update date:2022-08-30
Topics:
Benson, Helen
Bones, Karen
Churchill, Gwydion
Ford, Gair
Frodsham, Lianne
Janbon, Sophie
Millington, Fiona
Powell, Lyn
Raw, Steven A.
Reid, Julie
Stark, Andrew
Steven, Alan
Early chemical development studies into the best way of assembling AZD9742, an antibacterial drug candidate, have involved swapping the order of two reductive aminations. The orthogonally functionalized aminopiperidine partner for these couplings is now enantioselectively synthesized using ruthenium-catalyzed asymmetric hydrogenation. The challenge of controlling defluorination through an appropriate catalyst choice has hitherto prevented this revised sequence from reaching its full potential. However, it is still shown to allow access to the active pharmaceutical ingredient in a stereochemically pure form and has been demonstrated on a multikilogram scale. The reductive aminations in both the original and revised sequences provided different scale-up challenges, and the solutions implemented are described.
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