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Multigram-scale flow synthesis of the chiral key intermediate of (–)-paroxetine enabled by solvent-free heterogeneous organocatalysis† †Electronic supplementary information (ESI) available: Synthetic procedures, additional batch and flow reaction data, characterization data, copies of NMR spectra and HPLC chromatograms. See DOI: 10.1039/c9sc04752b
- Source :
- Chemical Science
- Publication Year :
- 2019
- Publisher :
- Royal Society of Chemistry, 2019.
-
Abstract
- The continuous flow synthesis of the chiral key intermediate of (–)-paroxetine is demonstrated via a solvent-free organocatalytic conjugate addition followed by a telescoped reductive amination–lactamization–amide/ester reduction sequence.<br />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.
- Subjects :
- Chemistry
polycyclic compounds
Subjects
Details
- Language :
- English
- ISSN :
- 20416539 and 20416520
- Volume :
- 10
- Issue :
- 48
- Database :
- OpenAIRE
- Journal :
- Chemical Science
- Accession number :
- edsair.pmid..........387b2e02a34d53ea7250e32fa30d8952