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Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines

(2010) ORGANIC & BIOMOLECULAR CHEMISTRY. 8(20). p.4514-4517
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Organization
Abstract
Synthetic routes toward new 5-amino- and 5-hydroxy-3,3-difluoropiperidines, which are of high interest as building blocks in medicinal chemistry, are described. The key step involves the N-halosuccinimide-induced cyclization of 2,2-difluoro-4-pentenylamines toward 5-halo-3,3-difluoropiperidines, which were used to synthesize 5-amino-3,3-difluoropiperidine. In a second strategy, iodolactonization of 2,2-difluoro-4-pentenoic acid gave the corresponding γ-lactone, which was transformed into 5-hydroxy-3,3-difluoropiperidine.
Keywords
CATALYZED CYCLIZATION, PIPERIDINES, UNSATURATED N-CHLOROAMINES, CATIONIC AMINYL RADICALS, DOUBLE-BONDS, ANALOGS, FLUORINE, PYRROLIDINES, REARRANGEMENT, CHEMISTRY

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Citation

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Chicago
Surmont, Riccardo, Guido Verniest, Jan Willem Thuring, Peter ten Holte, Frederik Deroose, and Norbert De Kimpe. 2010. “Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines.” Organic & Biomolecular Chemistry 8 (20): 4514–4517.
APA
Surmont, R., Verniest, G., Thuring, J. W., ten Holte, P., Deroose, F., & De Kimpe, N. (2010). Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(20), 4514–4517.
Vancouver
1.
Surmont R, Verniest G, Thuring JW, ten Holte P, Deroose F, De Kimpe N. Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines. ORGANIC & BIOMOLECULAR CHEMISTRY. 2010;8(20):4514–7.
MLA
Surmont, Riccardo, Guido Verniest, Jan Willem Thuring, et al. “Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines.” ORGANIC & BIOMOLECULAR CHEMISTRY 8.20 (2010): 4514–4517. Print.
@article{1055927,
  abstract     = {Synthetic routes toward new 5-amino- and 5-hydroxy-3,3-difluoropiperidines, which are of high interest as building blocks in medicinal chemistry, are described. The key step involves the N-halosuccinimide-induced cyclization of 2,2-difluoro-4-pentenylamines toward 5-halo-3,3-difluoropiperidines, which were used to synthesize 5-amino-3,3-difluoropiperidine. In a second strategy, iodolactonization of 2,2-difluoro-4-pentenoic acid gave the corresponding \ensuremath{\gamma}-lactone, which was transformed into 5-hydroxy-3,3-difluoropiperidine.},
  author       = {Surmont, Riccardo and Verniest, Guido and Thuring, Jan Willem and ten Holte, Peter and Deroose, Frederik and De Kimpe, Norbert},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {CATALYZED CYCLIZATION,PIPERIDINES,UNSATURATED N-CHLOROAMINES,CATIONIC AMINYL RADICALS,DOUBLE-BONDS,ANALOGS,FLUORINE,PYRROLIDINES,REARRANGEMENT,CHEMISTRY},
  language     = {eng},
  number       = {20},
  pages        = {4514--4517},
  title        = {Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines},
  url          = {http://dx.doi.org/10.1039/C0OB00231C},
  volume       = {8},
  year         = {2010},
}

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