280565-80-2Relevant articles and documents
A practical procedure for the resolution of (+)- and (-)-tramadol
Itov, Zinovy,Meckler, Harold
, p. 291 - 294 (2000)
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.