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Molecules 2018, 23(9), 2206; https://doi.org/10.3390/molecules23092206

A New Chemoenzymatic Synthesis of the Chiral Key Intermediate of the Antiepileptic Brivaracetam

1
Department of Medical Biotechnology and Translational Medicine, Università degli Studi di Milano, Via Saldini 50, 20133 Milano, Italy
2
Chemical-Pharmaceutical Consulting and IP Management, Viale Giovanni da Cermenate 58, 20141 Milano, Italy
*
Authors to whom correspondence should be addressed.
Received: 26 July 2018 / Revised: 23 August 2018 / Accepted: 29 August 2018 / Published: 31 August 2018
(This article belongs to the Section Organic Chemistry)
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Abstract

Brivaracetam is a new anticonvulsant compound, recently approved as an antiepileptic drug. This drug substance presents a 4-substituted pyrrolidone structure: the (4R)-configuration of the stereocenter present on the heterocyclic ring is the main target of the synthesis. The described method allows to prepare the suitable optically pure 2-substituted primary alcohol by means of a Pseudomonas fluorescens lipase-catalyzed transesterification. The obtained (2R)-alcohol was easily transformed into the (3R)-3-propylbutyrolactone, an advanced intermediate of brivaracetam. The described synthetic pathway is completed with the chromatographic methods and the NMR analyses necessary to establish the chemical and the optical purity of the intermediates and of the final lactone. View Full-Text
Keywords: biocatalysis; lipase; irreversible transesterification; (3R)-3-propylbutyrolactone biocatalysis; lipase; irreversible transesterification; (3R)-3-propylbutyrolactone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ciceri, S.; Grisenti, P.; Reza Elahi, S.; Ferraboschi, P. A New Chemoenzymatic Synthesis of the Chiral Key Intermediate of the Antiepileptic Brivaracetam. Molecules 2018, 23, 2206.

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