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Synthesis of 4-substituted 3,3-difluoropiperidines

(2010) JOURNAL OF ORGANIC CHEMISTRY. 75(3). p.929-932
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Organization
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.
Keywords
ETHYL BROMODIFLUOROACETATE, fluorine, BIOLOGICAL EVALUATION, MEDICINAL CHEMISTRY, ISONIPECOTIC ACIDS, COPPER-POWDER, INHIBITORS, FLUORINATION, ANALOGS, RING, piperidine

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Citation

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MLA
Surmont, Riccardo, et al. “Synthesis of 4-Substituted 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 3, 2010, pp. 929–32, doi:10.1021/jo902164z.
APA
Surmont, R., Verniest, G., Thuring, J. W., Macdonald, G., Deroose, F., & De Kimpe, N. (2010). Synthesis of 4-substituted 3,3-difluoropiperidines. JOURNAL OF ORGANIC CHEMISTRY, 75(3), 929–932. https://doi.org/10.1021/jo902164z
Chicago author-date
Surmont, Riccardo, Guido Verniest, Jan Willem Thuring, Gregor Macdonald, Frederik Deroose, and Norbert De Kimpe. 2010. “Synthesis of 4-Substituted 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY 75 (3): 929–32. https://doi.org/10.1021/jo902164z.
Chicago author-date (all authors)
Surmont, Riccardo, Guido Verniest, Jan Willem Thuring, Gregor Macdonald, Frederik Deroose, and Norbert De Kimpe. 2010. “Synthesis of 4-Substituted 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY 75 (3): 929–932. doi:10.1021/jo902164z.
Vancouver
1.
Surmont R, Verniest G, Thuring JW, Macdonald G, Deroose F, De Kimpe N. Synthesis of 4-substituted 3,3-difluoropiperidines. JOURNAL OF ORGANIC CHEMISTRY. 2010;75(3):929–32.
IEEE
[1]
R. Surmont, G. Verniest, J. W. Thuring, G. Macdonald, F. Deroose, and N. De Kimpe, “Synthesis of 4-substituted 3,3-difluoropiperidines,” JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 3, pp. 929–932, 2010.
@article{872196,
  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.}},
  author       = {{Surmont, Riccardo and Verniest, Guido and Thuring, Jan Willem and Macdonald, Gregor and Deroose, Frederik and De Kimpe, Norbert}},
  issn         = {{0022-3263}},
  journal      = {{JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{ETHYL BROMODIFLUOROACETATE,fluorine,BIOLOGICAL EVALUATION,MEDICINAL CHEMISTRY,ISONIPECOTIC ACIDS,COPPER-POWDER,INHIBITORS,FLUORINATION,ANALOGS,RING,piperidine}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{929--932}},
  title        = {{Synthesis of 4-substituted 3,3-difluoropiperidines}},
  url          = {{http://dx.doi.org/10.1021/jo902164z}},
  volume       = {{75}},
  year         = {{2010}},
}

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