Impact of Entropic Effects in the Classical Resolution of a 2-Arylpyrrolidine
| Autor: | David M. Barnes, Jufang Barkalow, Yong Chen, Francis A. J. Kerdesky, John E. Hengeveld, Anthony R. Haight, Bryan Macri, Ashok K. Gupta, Agnes Pal, Brian J. Kotecki |
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| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
Organic Chemistry Thermodynamics Salt (chemistry) Crystal structure law.invention chemistry.chemical_compound chemistry law Tartaric acid Racemic mixture Organic chemistry Physical and Theoretical Chemistry Crystallization Enantiomer Enantiomeric excess Solid solution |
| Zdroj: | Organic Process Research & Development. 13:225-229 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/op800242y |
| Popis: | The impact of entropic effects on the classical salt resolution of a 2-arylpyrrolidine is described. We have found that the crystallization of a racemic mixture of the base with tartaric acid led to a salt in which the undesired enantiomer is incorporated into the crystal lattice as a solid solution. The product enantiomer ratio was later determined to be at the thermodynamic well when the racemate is crystallized. In order to circumvent this effect, an efficient two-crystallization resolution was developed. The bulk of the undesired enantiomer is removed in the first crystallization so that the second crystallization can result in material of acceptable optical purity. |
| Databáze: | OpenAIRE |
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