Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors

An alternative and practical synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile was achieved. Reaction of L-proline with chloroacetyl chloride was followed by conversion of the carboxylic acid moiety of the resulting N-acylated product into the carbonitrile via the corresponding amide int...

Descripción completa

Detalles Bibliográficos
Autores principales: Singh, Santosh Kumar, Manne, Narendra, Pal, Manojit
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486489/
https://www.ncbi.nlm.nih.gov/pubmed/18941490
http://dx.doi.org/10.3762/bjoc.4.20
_version_ 1782158110273568768
author Singh, Santosh Kumar
Manne, Narendra
Pal, Manojit
author_facet Singh, Santosh Kumar
Manne, Narendra
Pal, Manojit
author_sort Singh, Santosh Kumar
collection PubMed
description An alternative and practical synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile was achieved. Reaction of L-proline with chloroacetyl chloride was followed by conversion of the carboxylic acid moiety of the resulting N-acylated product into the carbonitrile via the corresponding amide intermediate. The synthesized pyrrolidine derivative was utilized to prepare DPP-IV inhibitor Vildagliptin.
format Text
id pubmed-2486489
institution National Center for Biotechnology Information
language English
publishDate 2008
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-24864892008-10-20 Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors Singh, Santosh Kumar Manne, Narendra Pal, Manojit Beilstein J Org Chem Full Research Paper An alternative and practical synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile was achieved. Reaction of L-proline with chloroacetyl chloride was followed by conversion of the carboxylic acid moiety of the resulting N-acylated product into the carbonitrile via the corresponding amide intermediate. The synthesized pyrrolidine derivative was utilized to prepare DPP-IV inhibitor Vildagliptin. Beilstein-Institut 2008-06-12 /pmc/articles/PMC2486489/ /pubmed/18941490 http://dx.doi.org/10.3762/bjoc.4.20 Text en Copyright © 2008, Singh et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Singh, Santosh Kumar
Manne, Narendra
Pal, Manojit
Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title_full Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title_fullStr Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title_full_unstemmed Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title_short Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
title_sort synthesis of (s)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: a key intermediate for dipeptidyl peptidase iv inhibitors
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2486489/
https://www.ncbi.nlm.nih.gov/pubmed/18941490
http://dx.doi.org/10.3762/bjoc.4.20
work_keys_str_mv AT singhsantoshkumar synthesisofs12chloroacetylpyrrolidine2carbonitrileakeyintermediatefordipeptidylpeptidaseivinhibitors
AT mannenarendra synthesisofs12chloroacetylpyrrolidine2carbonitrileakeyintermediatefordipeptidylpeptidaseivinhibitors
AT palmanojit synthesisofs12chloroacetylpyrrolidine2carbonitrileakeyintermediatefordipeptidylpeptidaseivinhibitors

Ejemplares similares