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Synthesis of the Brivaracetam Employing Asymmetric Photocatalysis and Continuous Flow Conditions

By Franco, Marcelo S.; Silva, Rodrigo C.; Rosa, Gabriel H. S.; Flores, Lara M.; Oliveira, Kleber T. de; Assis, Francisco F. de

View Resource (DOI)

Category

Peer-reviewed journal

Published on CMKC

Abstract

An original total synthesis of the antiepileptic drug brivaracetam (BRV) is reported. The key step in the synthesis consists of an enantioselective photochemical Giese addition, promoted by visible-light and the chiral bifunctional photocatalyst Δ-RhS. Continuous flow conditions were employed to improve the efficiency and allow an easy scale-up of the enantioselective photochemical reaction step. The intermediate obtained from the photochemical step was converted into BRV by two different pathways, followed by one alkylation and amidation, thus giving the desired active pharmaceutical ingredients (API) in 44% overall yield, 9:1 diastereoisomeric ratio (dr) and >99:1 enantiomeric ratio (er).

Journal

ACS Omega. Volume 8, 2023, 23008–23016

DOI

10.1021/acsomega.3c02134

Type of publication

Peer-reviewed journal

Affiliations

  • Universidade Federal de Santa Catarina
  • Universidade Federal de São Carlos

Article Classification

Research Article

Classification Areas

  • Intermediate
  • API

Tags

  1. alkylation
  2. amidation
  3. API
  4. bifunctional photocatalyst
  5. Brivaracetam
  6. Enantioselective synthesis
  7. Giese addition
  8. Intermediate
  9. Research Article