Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy

Autor:	Nicolas S. Suveges, Rodrigo O. M. A. de Souza, Bernhard Gutmann, C. Oliver Kappe
Rok vydání:	2017
Předmět:	chemistry.chemical_classification 010405 organic chemistry Ropivacaine Organic Chemistry Mepivacaine Flow chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Aldehyde Reductive amination 0104 chemical sciences chemistry.chemical_compound chemistry Microwave chemistry Amide medicine Organic chemistry Physical and Theoretical Chemistry medicine.drug
Zdroj:	European Journal of Organic Chemistry. 2017:6511-6517
ISSN:	1434-193X
DOI:	10.1002/ejoc.201700824
Popis:	Herein we report a convenient, fast, and high-yielding method for the generation of the racemic amide anaesthetics mepivacaine, ropivacaine, and bupivacaine. Coupling of α-picolinic acid and 2,6-xylidine under sealed-vessel microwave conditions generates the intermediate amide after a reaction time of only 5 min at 150 °C. Subsequent reaction in a continuous-flow high-pressure hydrogenator (H-Cube ProTM) in the presence of the respective aldehyde directly converts the intermediate to the final amide anaesthetics in a continuous, integrated, multi-step ring-hydrogenation/reductive amination protocol. Merits and limitations of the protocol are discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e9ea76948fcb489f62877ec8d579f860 https://doi.org/10.1002/ejoc.201700824 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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