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BIBTEX RIS

Synthesis of the Brivaracetam Employing Asymmetric Photocatalysis and Continuous Flow Conditions

2023; American Chemical Society; Volume: 8; Issue: 25 Linguagem: Inglês

10.1021/acsomega.3c02134

ISSN

2470-1343

Autores

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

Tópico(s)

Catalytic C–H Functionalization Methods

Resumo

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).

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