(2S,5R)-1-Methyl-5-phenylpyrrolidin-2-yl]diphenylmethanol

Julio Zukerman-Schpector,Diogo S Lüdtke,Angélica Venturini Moro,Carlos Roque D Correia,Edward R T Tiekink

doi:10.1107/s1600536811023403

Abstract

In the title compound, C24H25NO, the phenyl and diphenylmethanol substituents are syn to each other. The pyrrolidine ring has an envelope conformation with the flap atom being the C atom bearing the phenyl substituent. The hydroxy group forms an intramolecular hydrogen bond with the pyrrolidine N atom, and the phenyl rings lie to same side of the molecule. The crystal packing features C—H⋯π interactions. Two slightly displaced co-planar orientations were found for one of the phenyl rings; the major component had a site-occupancy factor of 0.782 (15).

Highlights

In the title compound, C24H25NO, the phenyl and diphenylmethanol substituents are syn to each other
N atom, and the phenyl rings lie to same side of the molecule
2003) we have recently described a new chiral ligand for the highly enantioselective addition of arylzinc reagents to aldehydes

Summary

Bruker APEXII CCD diffractometer

Refinement a Departmento de Quımica, Universidade Federal de São Carlos, CP 676, 13565-905. São Carlos-SP, Brazil, bInstituto de Quımica, Universidade Estadual de Campinas, UNICAMP, CP 6154, CEP 13084-917 Campinas, Brazil, cInstituto de Quımica, Universidade Federal, de Rio Grande do Sul, UFRGS, Av. Bento Gonçalves 9500, 91501-570 Porto Alegre, RS, Brazil, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia. Cg is the centroid of the C6–C11 ring. Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.004 Å; disorder in main residue; R factor = 0.038; wR factor = 0.092; data-to-parameter ratio = 8.9. The pyrrolidine ring has an envelope conformation with the flap atom being the C atom bearing the phenyl substituent. N atom, and the phenyl rings lie to same side of the molecule. Two slightly displaced co-planar orientations were found for one of the phenyl rings; the major component had a site-occupancy factor of 0.782 (15)

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Findings

Graphite monochromator φ and ω scans