Resolution of (±)-nipecotic acid ((±)-3-piperidinecarboxylic acid) by separation of palladium (II) diastereomers containing orthometallated (S)-(−)-1-[1-(dimethylamino) …

…, DCR Hockless, NL Kilah, RC Mayadunne…

Index: Gugger, Paul A.; Hockless, David C.R.; Kilah, Nathan L.; Mayadunne, Renuka C.; Wild, S. Bruce Tetrahedron Asymmetry, 2008 , vol. 19, # 15 p. 1810 - 1812

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Citation Number: 4

Abstract

An efficient resolution of (±)-nipecotic acid has been achieved by the fractional crystallization of internally diastereomeric palladium (II) complexes containing the chelated carboxylate and orthometallated (S)-(−)-1-[1-(dimethylamino) ethyl] naphthalene. The configurationally pure enantiomers of the acid were recovered from the individual diastereomers of the complex by treatment with hydrochloric acid, which also regenerated the palladium (II) ...