Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines
- Author
- Riccardo Surmont (UGent) , Guido Verniest (UGent) , Jan Willem Thuring, Peter ten Holte, Frederik Deroose and Norbert De Kimpe (UGent)
- 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
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-1055927
- MLA
- Surmont, Riccardo, et al. “Synthesis of 5-Amino- and 5-Hydroxy-3,3-Difluoropiperidines.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 8, no. 20, 2010, pp. 4514–17, doi:10.1039/C0OB00231C.
- 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. https://doi.org/10.1039/C0OB00231C
- Chicago author-date
- 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): 4514–17. https://doi.org/10.1039/C0OB00231C.
- Chicago author-date (all authors)
- 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. doi:10.1039/C0OB00231C.
- 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.
- IEEE
- [1]R. Surmont, G. Verniest, J. W. Thuring, P. ten Holte, F. Deroose, and N. De Kimpe, “Synthesis of 5-amino- and 5-hydroxy-3,3-difluoropiperidines,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 8, no. 20, pp. 4514–4517, 2010.
@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 γ-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}}, keywords = {{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://doi.org/10.1039/C0OB00231C}}, volume = {{8}}, year = {{2010}}, }
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