A Practical Procedure for the Resolution of (+)- and (−)-Tramadol

Autor:	Harold Meckler, Zinovy Itov and
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Hydrochloride Organic Chemistry Inorganic chemistry Cyclohexanol Salt (chemistry) Free base Mandelic acid Kinetic resolution chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Enantiomer Enantiomeric excess
Zdroj:	Organic Process Research & Development. 4:291-294
ISSN:	1520-586X 1083-6160
Popis:	A practical procedure for the efficient resolution of cis-tramadol [cis-2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol] has been developed. This process was based on the observation that cis-tramadol free base selectively formed mandelic acid salts at different rates, affording a readily scalable kinetic resolution of each enantiomer. The key to the process was the observation that the resolving salt needed to be broken and re-formed to ultimately improve the optical purity. The mandalate salt of each cis-enantiomer was found to be >99% optically pure after three cycles through the salt formation process. A sample of each mandelate salt enantiomer was successfully converted to the known, optically active hydrochloride salt.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::16abaa1f5254d9f40103ae74a38df0ea https://doi.org/10.1021/op000281v Zobrazit plný text záznamu