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Development of an Enantioselective [3 + 2] Cycloaddition To Synthesize the Pyrrolidine Core of ABBV-3221 on Multikilogram Scale

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posted on 2019-09-19, 14:03 authored by John Hartung, Stephen N. Greszler, Russell C. Klix, Jeffrey M. Kallemeyn
The tetrasubstituted pyrrolidine core of ABBV-3221 was synthesized by catalytic, enantioselective cycloaddition. A Cu­(I) catalyst system was identified as ideal for further development, which gave a 78% yield of 99% purity product after optimization. The processes of catalyst selection, optimization, and crystallization of the cycloaddition product are described herein.

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