4.6 Article

Practical large-scale synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate: Atom economical self-hydrogenolysis of a crystalline borane-benzylamine adduct

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ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 6, 期 1, 页码 42-48

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AMER CHEMICAL SOC
DOI: 10.1021/op0102161

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An efficient four-step sequence has been developed for the synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate starting from inexpensive N-benzyhnaleimide. This approach features a novel N-debenzylation procedure that utilizes the corresponding borane-benzylamine complex as an internal hydrogen-transfer source. This palladium-catalyzed tandem protonolysis/hydrogenolysis allows cleavage of the borane-amine adduct and debenzylation in a single operation.

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