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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 contribution
posted on 2023-05-17, 17:18 authored by Gugger, PA, Hockless, DCR, Nathan KilahNathan Kilah, Mayadunne, RC, Wild, SBAn 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.
History
Publication title
Tetrahedron: AsymmetryVolume
19Issue
15Pagination
1810-1812ISSN
0957-4166Department/School
School of Natural SciencesPublisher
Pergamon-Elsevier Science LtdPlace of publication
The Boulevard, Langford Lane, Kidlington, Oxford, England, Ox5 1GbRights statement
Copyright 2008 Elsevier Ltd.Repository Status
- Restricted