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  • Title: Synthesis of 4-substituted 3,3-difluoropiperidines.
    Author: Surmont R, Verniest G, Thuring JW, Macdonald G, Deroose F, De Kimpe N.
    Journal: J Org Chem; 2010 Feb 05; 75(3):929-32. PubMed ID: 20050617.
    Abstract:
    Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.
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