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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
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author Zhu, Huichun
Plewe, Michael B.
Rheingold, Arnold L.
Moore, Curtis
Yanovsky, Alex
author_facet Zhu, Huichun
Plewe, Michael B.
Rheingold, Arnold L.
Moore, Curtis
Yanovsky, Alex
author_sort Zhu, Huichun
collection PubMed
description 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.
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spelling pubmed-29800012010-12-30 (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 Zhu, Huichun Plewe, Michael B. Rheingold, Arnold L. Moore, Curtis Yanovsky, Alex Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2009-12-16 /pmc/articles/PMC2980001/ /pubmed/21580061 http://dx.doi.org/10.1107/S1600536809053331 Text en © Zhu et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ 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.
spellingShingle Organic Papers
Zhu, Huichun
Plewe, Michael B.
Rheingold, Arnold L.
Moore, Curtis
Yanovsky, Alex
(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
title (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
title_full (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
title_fullStr (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
title_full_unstemmed (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
title_short (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
title_sort (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
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980001/
https://www.ncbi.nlm.nih.gov/pubmed/21580061
http://dx.doi.org/10.1107/S1600536809053331
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