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Synthesis of the Brivaracetam Employing Asymmetric Photocatalysis and Continuous Flow Conditions

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Author(s):
Franco, Marcelo S. ; Silva, Rodrigo C. ; Rosa, Gabriel H. S. ; Flores, Lara M. ; de Oliveira, Kleber T. ; de Assis, Francisco F.
Total Authors: 6
Document type: Journal article
Source: ACS OMEGA; v. 8, n. 25, p. 9-pg., 2023-06-14.
Abstract

An original totalsynthesis of the antiepileptic drug brivaracetam(BRV) is reported. The key step in the synthesis consists of an enantioselectivephotochemical Giese addition, promoted by visible-light and the chiralbifunctional photocatalyst Delta-RhS. Continuous flowconditions were employed to improve the efficiency and allow an easyscale-up of the enantioselective photochemical reaction step. Theintermediate obtained from the photochemical step was converted intoBRV by two different pathways, followed by one alkylation and amidation,thus giving the desired active pharmaceutical ingredients (API) in44% overall yield, 9:1 diastereoisomeric ratio (dr) and >99:1 enantiomericratio (er). (AU)

FAPESP's process: 20/06874-6 - Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants
FAPESP's process: 19/27176-8 - Asymmetric photocatalysis applied to the synthesis of Brivaracetam: synthetic approaches employing enabling technologies for chemical synthesis
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants
FAPESP's process: 20/04114-4 - Studies on photooxygenation reactions and chemical transformations in (+)-(alfa)-pinene to (-)-pinocarvone and (-)-aritasone under continuous flow conditions
Grantee:Gabriel Hiroshi Seki Rosa
Support Opportunities: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 18/00879-6 - Arylation reactions of heterocycles photocatalysed by porphyrins in both batch and continuous flow conditions.
Grantee:Rodrigo Costa e Silva
Support Opportunities: Scholarships in Brazil - Doctorate