Nucleophilic Ring-Opening Reactions of Morpholin-2-ones. A Resolution of dl-(Secondary-alkyl)amines

Article abstract of DOI:10.1021/jo00265a015

The alcoholysis of morpholin-2-ones yielded an equilibrium mixture of morpholin-2-one and the corresponding hydroxy ester.The equilibrium constants for the methanolysis of several sustituted morpholin-2-ones were determined.Treatment of optically active morpholin-2-ones with (secondary-alkyl)amines resulted in stereoselective ring opening to afford hydroxy amides with up to 30percent de.Hydrolysis of one such hydroxy amide regenerated the optically active (secondary-alkyl)amine and the morpholin-2-one.