Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry

Indrawan McAlpine; Michelle Tran-Dubé; Fen Wang; Stephanie Scales; Jean Matthews; Michael R Collins; Sajiv K Nair; Mary Nguyen; Jianwei Bian; Luis Martinez Alsina; Jianmin Sun; Jiaying Zhong; Joseph S Warmus; Brian T O’Neill

doi:10.1021/acs.joc.5b00853

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Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry

Journal article

Peer reviewed

Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry

Indrawan McAlpine, Michelle Tran-Dubé, Fen Wang, Stephanie Scales, Jean Matthews, Michael R Collins, Sajiv K Nair, Mary Nguyen, Jianwei Bian, Luis Martinez Alsina, …

Journal of organic chemistry, Vol.80(14), pp.7266-7274

07/17/2015

DOI: 10.1021/acs.joc.5b00853

PMID: 26057617

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Abstract

Here, we report accessing small 3-fluoropyrrolidines and 3,3-difluoropyrrolidines through a 1,3-dipolar cycloaddition with a simple azomethine ylide and a variety of vinyl fluorides and vinyl difluorides. We demonstrate that vinyl fluorides within α,β-unsaturated, styrenyl and even enol ether systems can participate in the cycloaddition reaction. The vinyl fluorides are relatively easy to synthesize through a variety of methods, making the 3-fluoropyrrolidines very accessible.

Details

Title: Subtitle: Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry
Creators: Indrawan McAlpine - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Michelle Tran-Dubé - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Fen Wang - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Stephanie Scales - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Jean Matthews - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Michael R Collins - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Sajiv K Nair - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Mary Nguyen - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 10770 Science Center Drive, San Diego, California 92121, United States
Jianwei Bian - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Luis Martinez Alsina - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Jianmin Sun - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Jiaying Zhong - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Joseph S Warmus - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Brian T O’Neill - Pfizer Worldwide Medicinal Chemistry, Pfizer Research & Development, 445 Eastern Point Road, Groton, Connecticut 06340, United States
Resource Type: Journal article
Publication Details: Journal of organic chemistry, Vol.80(14), pp.7266-7274
DOI: 10.1021/acs.joc.5b00853
PMID: 26057617
NLM abbreviation: J Org Chem
ISSN: 0022-3263
eISSN: 1520-6904
Language: English
Date published: 07/17/2015
Academic Unit: Endocrinology and Metabolism; Internal Medicine
Record Identifier: 9984094350202771

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