Route design and process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, and optimization of the imidazole cyclization are described.

Upadacitinib: Process development of a JAK1 inhibitor

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