Synthesis of 4-substituted 3,3-difluoropiperidines

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 929-932

  Surmont, Riccardo ^a,c   Verniest, Guido ^a,c   Thuring, Jan Willem ^b   Macdonald, Gregor ^b   Deroose, Frederik ^b   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^c RESEARCH FOUNDATION FLANDERS FWO   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE REDUCTION; BUILDING BLOCKES; HIGH POTENTIAL; MEDICINAL CHEMISTRY; SYNTHETIC STRATEGIES;

AMINO ACIDS; COPPER POWDER; ORGANIC ACIDS;

SYNTHESIS (CHEMICAL);

4 ALKOXYMETHYL 3,3 DIFLUOROPIPERIDINE DERIVATIVE; 4 BENZYLOXY 3,3 DIFLUOROPIPERIDINE; ACETIC ACID DERIVATIVE; ACRYLONITRILE; ETHYL BROMODIFLUOROACETATE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

AMINO ACIDS; COPPER; HYDROCARBONS, FLUORINATED; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 75749157765     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902164z     Document Type: Article

References (31)

1. (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991 and references cited therein.
2. (b) Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; John Wiley & Sons: Hoboken, NJ, 2008.
3. (c) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
4. (d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
5. (e) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
6. (f ) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
7. Van Hende, E.; Verniest, G.; Thuring, J. W.; Macdonald, G.; Deroose, F.; De Kimpe, N. Synlett 2009, 1765.
8. Surmont, R.; Verniest, G.; De Weweire, A.; Thuring, J. W.; Macdonald, G.; Deroose, F.; De Kimpe, N. Synlett 2009, 1933.
9. Verniest, G.; Surmont, R.; Van Hende, E.; De Weweire, A.; Deroose, F.; Thuring, J. W.; De Kimpe, N. J. Org. Chem. 2008, 73, 5458 and references cited therein.
10. (a) Masuya, K.;Yokokawa, F.; Irie, O.; Nihonyanagi, A.; Toyao, A.; Ehara, T.; Konishi, K.; Kanazawa, T.; Suzuki, M. PCT Int. Appl.WO2006094763, 2006; Chem. Abstr. 2006, 145, 335938.
11. (b) Castro Pineiro, J. L.; Dinnell, K.; Elliot, J. M.; Hollingworth, G. J.; Shaw, D. E.; Swain, C. J. PCT Int. Appl. WO 2001087838, 2001; Chem. Abstr. 2001, 136, 5907.
12. (a) Krehan, D.; Frølund, B.; Krogsgaard-Larsen, P.; Kehler, J.; Johnston, G. A. R.; Chebib, M. Neurochem. Int. 2003, 42, 561.
13. (b) Antane, S. Synth. Commun. 2003, 33, 2145 and references cited therein.
14. (c) Fan, J.; Fahr, B.; Stockett, D.; Chan, E.; Cheeti, S.; Serafimova, I.; Lu, Y.; Pham, P.; Walker, D. H.; Hoch, U.; Choong, I. C. Bioorg. Med. Chem. Lett. 2008, 18, 6236.
15. (d) Crider, A. M.; Tita, T. T.; Wood, J. D.; Hinko, C. N. J. Pharm. Sci. 1982, 71, 1214.
16. Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2005, 105, 529.
17. van Niel, M. B.; Collins, I.; Beer, M. S.; Broughton, H. B.; Cheng, S. K. F.; Goodacre, S. C.; Heald, A.; Locker, K. L.; MacLeod, A. M.; Morrison, D.; Moyes, C. R.; O'Connor, D.; Pike, A.; Rowley, M.; Russel, N.; Sohal, B.; Stanton, J. A.; Thomas, S.; Verrier, H.; Watt, A. P.; Castro, J. L. J. Med. Chem. 1999, 42, 2087.
18. Marmsaeter, F. P.; Munson, M. C.; Rizzi, J. P.; Robinson, J. E.; Schlachter, S. T.; Topalov, G. T.; Zhao, Q.; Lyssikatos, J. P. PCT Int. Appl. WO 2008121687, 2008; Chem. Abstr. 2008, 149, 448388.
19. Huang, H.; Hutta, D. A.; Rinker, J. M.; Hu, H.; Parsons, W. H.; Schubert, C.; DesJarlais, R. L.; Crysler, C. S.; Chaikin, M. A.; Donatelli, R. R.; Chen, Y.; Cheng, D.; Zhou, Z.; Yurkow, E.; Manthey, C. L.; Player, M. R. J. Med. Chem. 2009, 52, 1081.
20. Stanton, M. G.; Munoz, B.; Sloman, D. L.; Hubbs, J.; Hamblett, C. PCT Int. Appl. WO 2008030391, 2008; Chem. Abstr. 2008, 148, 331574.
21. Wang, R.-W.; Qiu, X.-L.; Bols, M.; Ortega-Caballero, F.; Qing, F.-L. J. Med. Chem. 2006, 49, 2989.
22. Beeler, A. B.; Gadepalli, R. S. V. S.; Steyn, S.; Castagnoli, N.; Rimoldi, J. M. Bioorg. Med. Chem. 2003, 11, 5229.
23. (a) Sato, K.; Tamura, M.; Tamoto, K.; Omote, M.; Ando, A.; Kumadaki, I. Chem. Pharm. Bull. 2000, 48, 1023.
24. (b) Laurent, S.; Chen, H.; Bedu, S.; Ziarelli, F.; Peng, L.; Zhang, C.-C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 9907.
25. Sato, K.; Nakazato, S.; Enko, H.; Tsujita, H.; Fujita, K.; Yamamoto, T.; Omote, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 2003, 121, 105.
26. (a) Kikuchi, H.; Satoh, H.; Fukutomi, R.; Inomata, K.; Suzuki, M.; Hagihara, K.; Arai, T.; Mino, S.; Eguchi, H. PCT Int. Appl. WO 9531442, 1995; Chem. Abstr. 1995, 124, 232479.
27. (b) Kuwamura, T.; Takahashi, H. Bull. Chem. Soc. Jpn. 1969, 42, 1345.
28. (c) Julia, M.; Tchernoff, G. Bull. Soc. Chim. Fr. 1954, 474.
29. (d) Iranpoor, N.; Shekarriz, M. Synth. Commun. 1999, 29, 2249.
30. (e) Itadani, S.; Hashimoto, K.; Shirahama, H. Heterocycles 1998, 49, 105.
31. Murtagh, J. E.; McCooey, S. H.; Connon, S. Chem. Commun. 2005,