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Resolution of (+-)-nipecotic acid ((+-)-3-piperidinecarboxylic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(-)-1-[1-(dimethylamino)ethyl]naphthalene
journal contributionposted on 2023-05-17, 17:18 authored by Gugger, PA, Hockless, DCR, Nathan KilahNathan Kilah, Mayadunne, RC, Wild, SB
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) resolving agent. The crystal structure of the less-soluble diastereomer of the complex has been determined.
Publication titleTetrahedron: Asymmetry
Department/SchoolSchool of Natural Sciences
PublisherPergamon-Elsevier Science Ltd
Place of publicationThe Boulevard, Langford Lane, Kidlington, Oxford, England, Ox5 1Gb
Rights statementCopyright 2008 Elsevier Ltd.