Cargando…
(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)...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1782191553538686976 |
---|---|
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. |
format | Text |
id | pubmed-2980001 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT zhuhuichun 3as7as5s333trifluoro2methoxy2phenylpropanoyl234567hexahydro1hpyrrolo34cpyridin32honemonohydrate AT plewemichaelb 3as7as5s333trifluoro2methoxy2phenylpropanoyl234567hexahydro1hpyrrolo34cpyridin32honemonohydrate AT rheingoldarnoldl 3as7as5s333trifluoro2methoxy2phenylpropanoyl234567hexahydro1hpyrrolo34cpyridin32honemonohydrate AT moorecurtis 3as7as5s333trifluoro2methoxy2phenylpropanoyl234567hexahydro1hpyrrolo34cpyridin32honemonohydrate AT yanovskyalex 3as7as5s333trifluoro2methoxy2phenylpropanoyl234567hexahydro1hpyrrolo34cpyridin32honemonohydrate |