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(3aS,7aS)-5-[(S)-3,3,3-Trifluoro-2-meth­oxy-2-phenyl­propano­yl]-2,3,4,5,6,7-hexa­hydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one monohydrate

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)...

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Detalles Bibliográficos
Autores principales: Zhu, Huichun, Plewe, Michael B., Rheingold, Arnold L., Moore, Curtis, Yanovsky, Alex
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980001/
https://www.ncbi.nlm.nih.gov/pubmed/21580061
http://dx.doi.org/10.1107/S1600536809053331
Descripción
Sumario: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, C(17)H(19)F(3)N(2)O(3)·H(2)O. 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.