The sustainable synthesis of levetiracetam by an enzymatic dynamic kinetic resolution and an ex-cell anodic oxidation

Sebastian Arndt, Birgit Grill, Helmut Schwab, Georg Steinkellner, Dominik Weis, Urska Pogorevcnik, Alexander Nauth, Karl Gruber, Till Opatz, Kai Donsbach, Siegfried R. Waldvogel, Margit Winkler

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

Levetiracetam is an active pharmaceutical ingredient widely used to treat epilepsy. We describe a new synthesis of levetiracetam by a dynamic kinetic resolution and a ruthenium-catalysed ex-cell anodic oxidation. For the enzymatic resolution, we tailored a high throughput screening method to identify Comamonas testosteroni nitrile hydratase variants with high (S)-selectivity and activity. Racemic nitrile was applied in a fed-batch reaction and was hydrated to (S)-(pyrrolidine-1-yl)butaneamide. For the subsequent oxidation to levetiracetam, we developed a ligand-free ruthenium-catalysed method at a low catalyst loading. The oxidant was electrochemically generated in 86% yield. This route provides a significantly more sustainable access to levetiracetam than existing routes. This journal is

Originalspracheenglisch
Seiten (von - bis)388-395
Seitenumfang8
FachzeitschriftGreen Chemistry
Jahrgang23
Ausgabenummer1
DOIs
PublikationsstatusVeröffentlicht - 7 Jan 2021

ASJC Scopus subject areas

  • !!Pollution
  • Umweltchemie

Fields of Expertise

  • Human- & Biotechnology

Fingerprint

Untersuchen Sie die Forschungsthemen von „The sustainable synthesis of levetiracetam by an enzymatic dynamic kinetic resolution and an ex-cell anodic oxidation“. Zusammen bilden sie einen einzigartigen Fingerprint.

Dieses zitieren