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Multigram-scale flow synthesis of the chiral key intermediate of (−)-paroxetine enabled by solvent-free heterogeneous organocatalysis

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Abstract

The catalytic enantioselective synthesis of the chiral key intermediate of the antidepressant (−)-paroxetine is demonstrated as a continuous flow process on multi-gram scale. The critical step is a solvent-free organocatalytic conjugate addition followed by a telescoped reductive amination–lactamization–amide/ester reduction sequence. Due to the efficient heterogeneous catalysts and the solvent-free or highly concentrated conditions applied, the flow method offers key advances in terms of productivity and sustainability compared to earlier batch approaches.

Graphical abstract: Multigram-scale flow synthesis of the chiral key intermediate of (−)-paroxetine enabled by solvent-free heterogeneous organocatalysis

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Publication details

The article was received on 20 Sep 2019, accepted on 18 Oct 2019 and first published on 18 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC04752B
Chem. Sci., 2019, Advance Article
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    Multigram-scale flow synthesis of the chiral key intermediate of (−)-paroxetine enabled by solvent-free heterogeneous organocatalysis

    S. B. Ötvös, M. A. Pericàs and C. O. Kappe, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC04752B

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