Scalable synthesis of 1-bicyclo[1.1.1]pentylamine via a hydrohydrazination reaction

Organic Letters

Volumn 13, Issue 17, 2011, Pages 4746-4748

  Bunker, Kevin D ^a   Sach, Neal W ^a   Huang, Qinhua ^a   Richardson, Paul F ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BICYCLO(1.1.1)PENTYLAMINE; 1-BICYCLO(1.1.1)PENTYLAMINE; AMINE; BICYCLO COMPOUND; HYDRALAZINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; BICYCLO COMPOUNDS; HYDRALAZINE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80052249648     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201883z     Document Type: Article

References (42)

1. Burkhard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 9052
2. Wuitschik, G.; Carreira, E. M.; Wagner, B.; Fischer, H.; Parrilla, I.; Schuler, F.; Rogers-Evans, M.; Müller, K. J. Med. Chem. 2010, 53, 3227
3. Duncton, M. A. J.; Estiarte, M. A.; Tan, D.; Kaub, C.; O'Mahony, D. J. R.; Johnson, R. J.; Cox, M.; Edwards, W. T.; Wan, M.; Kincaid, J. Org. Lett. 2008, 10, 3259
4. Stocks, M. J.; Wilden, G. R. H.; Pairaudeau, G.; Perry, M. W. D.; Steele, J.; Stonehouse, J. P. ChemMedChem 2009, 4, 800
5. Hamzik, P. J.; Brubaker, J. D. Org. Lett. 2010, 12, 1116
6. Guérot, C.; Tchitchanov, B. H.; Knust, H.; Carreira, E. M. Org. Lett. 2011, 13, 780
7. Duncton, M. A. J.; Estiarte, M. A.; Johnson, R. J.; Cox, M.; O'Mahony, D. J. R.; Edwards, W. T.; Kelly, M. G. J. Org. Chem. 2009, 74, 6354
8. Hossain, M. T.; Timberlake, J. W. J. Org. Chem. 2001, 66, 6282
9. Barbachyn, M. R.; Hutchinson, D. K.; Toops, D. S.; Reid, R. J.; Zurenko, G. E.; Yagi, B. H.; Schaadt, R. D.; Allison, J. W. Bioorg. Med. Chem. Lett. 1993, 3, 671
10. Brewer, P. G.; Runge, T. A.; Timko, J. M.; Veldman, T. J.; Walker, J. A. Preparation of 1-Bicyclopentylamine Hydrochloride, U85,879A - a Key Intermediate for the Syntheses of Quinolone Antibacterial Agents; TR1510-91-005; Upjohn: October 3, 1991.
11. Wiberg, K. B.; Williams, V. Z., Jr. J. Org. Chem. 1970, 35, 369
12. Della has prepared compound 1 from 1-carboxybicyclo[1.1.1]pentane in 34% using a modified Hoffmann rearrangement; see: Della, E. W.; Kasum, B.; Kirkbride, K. P. J. Am. Chem. Soc. 1987, 109, 2746
13. Wiberg, K. B.; Waddell, S. T. J. Am. Chem. Soc. 1990, 112, 2194
14. Gammill, R. B.; Bisaha, S. N.; Timko, J. M.; Judge, T. M.; Barbachyn, M. R.; Kim, K. S. Preparation of Antibacterial Quinolone and Naphthyridone Compounds (Upjohn Co., USA); WO 90/06307, June 14, 1990.
15. Bennett, M. J.; Zehnder, L. R.; Ninkovic, S.; Kung, P.-P.; Meng, J. J.; Huang, B. 2-Amino-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine Derivatives as HSP-90 Inhibitors and their Preparation, Pharmaceutical Compositions and use in the Treatment of Cancer (Pfizer Inc., USA); WO 2008/096218, Aug. 14, 2008.
16. Dessole, G.; Jones, P.; Bufi, L. L.; Muraglia, E.; Ontoria Ontoria, J. M.; Torrisi, C. Preparation of 1,2,4-Oxadiazole Substituted Piperidine and Piperazine Derivatives as SMO Antagonists (Istituto di Ricerche di Biologia Molecolare P. Angeletti S.p.A., Italy); WO 2010/013037, Feb. 4, 2010.
17. Kung, P.-P.; Meng, J. J. Preparation of Pyrazolylethoxyphenyl- pyrroloyrimidinamines as Heat Shock Protein-90 (HSP-90) Inhibitors (Pfizer Inc., USA); WO 2010/018481, Feb. 18 2010.
18. Levin, M. D.; Kaszynski, P.; Michl, J. Chem. Rev. 2000, 100, 169
19. Toops, D. S.; Barbachyn, M. R. J. Org. Chem. 1993, 58, 6505
20. Hossain, M. T.; Timberlake, J. W. J. Org. Chem. 2001, 66, 4409
21. Hassenrueck, K.; Murthy, G. S.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013
22. Mazal, C.; Paraskos, A. J.; Michl, J. J. Org. Chem. 1998, 63, 2116
23. Ayats, C.; Camps, P.; Font-Bardia, M.; Solans, X.; Vázquez, S. Tetrahedron 2007, 63, 8027
24. Banwell, M. G.; Chun, C.; Edwards, A. J.; Voegtle, M. M. Aust. J. Chem. 2003, 56, 861
25. Camps, P.; Lukach, A. E.; Rossi, R. A. J. Org. Chem. 2001, 66, 5366
26. Boukherroub, R.; Chatgilialoglu, C.; Manuel, G. Organometallics 1996, 15, 1508
27. Wiberg, K. B.; McMurdie, N. J. Am. Chem. Soc. 1994, 116, 11990
28. Della, E. W.; Lochert, I. J. Org. Prep. Proced. Int. 1996, 28, 411
29. Kaszynski, P.; Michl, J. Chem. Cyclopropyl Group 1995, 2, 773
30. Wiberg, K. B. Chem. Rev. 1989, 89, 975
31. Della, E. W.; Pigou, P. E.; Schiesser, C. H.; Taylor, D. K. J. Org. Chem. 1991, 56, 4659
32. Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693
33. Waser, J.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 5676
34. Waser, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 4099
35. For a review of hydroamination, see: Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795
36. Shtarev, A. B.; Pinkhassik, E.; Levin, M. D.; Stibor, I.; Michl, J. J. Am. Chem. Soc. 2001, 123, 3484
37. Adcock, W.; Krstic, A. R. Magn. Reson. Chem. 2000, 38, 115
38. Waser, J.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 8294
39. Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4519
40. Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 5758
41. Gaspar, B.; Carreira, E. M. J. Am. Chem. Soc. 2009, 131, 13214
42. Inoki, S.; Kato, K.; Isayama, S.; Mukaiyama, T. Chem. Lett. 1990, 1869