NDLI: (3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-meth-oxy-2-phenyl-propano-yl]-2,3,4,5,6,7-hexa-hydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate.

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(3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-meth-oxy-2-phenyl-propano-yl]-2,3,4,5,6,7-hexa-hydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate.

Content Provider	Europe PMC
Author	Zhu, Huichun Plewe, Michael B. Rheingold, Arnold L. Moore, Curtis Yanovsky, Alex
Copyright Year	2010
Abstract	rac-Benzyl 3-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate was separated by chiral chromatography, and one of the enantiomers ([α]22 D = +10°) was hydrogenated in the presence of Pd/C in methanol, producing octahydro-3H-pyrrolo[3,4-c]pyridin-3-one. The latter was reacted with (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride [(R)-(−)-Mosher acid chloride], giving rise to the title compound, C17H19F3N2O3·H2O. The present structure established the absolute configuration of the pyrrolopiperidine fragment based on the known configuration of the (R)-Mosher acid chloride. The piperidine ring has a somewhat distorted chair conformation and is cis-fused with the five-membered envelope-shaped ring; the plane of the exocyclic amide bond is approximately orthogonal to the plane of the phenyl ring, making a dihedral angle of 82.31 (3)°. The water molecule acts as an acceptor to the proton of the amino group in an N—H⋯O interaction, and as a double proton donor in O—H⋯O hydrogen bonds, generating infinite bands along the a axis.
Journal	Acta crystallographica. Section E, Structure Reports Online
Volume Number	66
PubMed Central reference number	PMC2980001
Issue Number	Pt 1
Issue Number	pt 1
PubMed reference number	21580061
e-ISSN	16005368
DOI	10.1107/s1600536809053331
Language	English
Publisher	International Union of Crystallography
Publisher Date	2009-12-16
Access Restriction	Open
Rights License	This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. © Zhu et al. 2010
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Materials Science

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