Investigation of Practical Routes for the Kilogram-Scale Production of cis-3-Methylamino-4-methylpiperidines

Autor:	Timothy D. White, Jay F. Stearns, Heather N. Frost, Ashwin M. Krishnan, James E. Phillips, Ruggeri Sally G, James L. Colony, Duane J. Mazur, Weiling Cai, Teresa W. Makowski, David H. Brown Ripin, Peter M. Kendall, James P. Hudspeth
Rok vydání:	2005
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone chemistry Organic Chemistry Pyridine Organic chemistry Piperidine Physical and Theoretical Chemistry Electrochemistry Reductive amination
Zdroj:	Organic Process Research & Development. 9:51-56
ISSN:	1520-586X 1083-6160
Popis:	Two routes for the synthesis of cis-N-protected-3-methylamino-4-methylpiperidine (3) were examined: a route hinging on the electrochemical oxidation of carbamate 1 to install a ketone at the 3 position of the piperidine followed by reductive amination (disconnection A), and a route involving the hydrogenation of an appropriately functionalized pyridine (disconnection B). While both routes to the desired compound were ultimately successful, the pyridine hydrogenation approach proved to be more amenable to kilogram-scale preparations due to the crystallinity and purity of intermediates in that route.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::10d7c980f02c5aa5a94d2e5d6999c2fb https://doi.org/10.1021/op049808k Zobrazit plný text záznamu