Document Detail


New entries toward 3,3-difluoropiperidines.
MedLine Citation:
PMID:  18547110     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable delta-chloro-alpha,alpha-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding delta-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction of the imino bond and subsequent intramolecular substitution of the chloride atom, new 3,3-difluoropiperidines were obtained in good yields. In addition, this methodology was applied to establish the first synthesis of N-protected 3,3-difluoropipecolic acid, a new fluorinated amino acid.
Authors:
Guido Verniest; Riccardo Surmont; Eva Van Hende; Arvid Deweweire; Frederik Deroose; Jan Willem Thuring; Norbert De Kimpe
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-06-12
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Jul 
Date Detail:
Created Date:  2008-07-14     Completed Date:  2008-09-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5458-61     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
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MeSH Terms
Descriptor/Qualifier:
Fluorine Compounds / chemical synthesis*,  chemistry
Molecular Structure
Piperidines / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Fluorine Compounds; 0/Piperidines

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