Organozirconium-mediated solution- and solid-phase synthesis of 3-benzyl pyrrolidines and other potentially neuroactive amines

Synlett

Volumn , Issue 19, 2006, Pages 3314-3318

  Hunter, Rupert A ^a   Macfarlane, Donald P S ^a   Whitby, Richard J ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Library; Neuroactive; Pyrrolidine; Solid phase; Zirconium

Indexed keywords

1 BENZYL 3 METHYL 4 (4 METHYLBENZYL)PYRROLIDINE; 3 BENZYL 4 METHYLPYRROLIDINE; 3 METHYL 4 (4 METHYLBENZYL)PYRROLIDINE; N BENZYL 3 METHYL 4 (4 METHYLBENZYL)PYRROLIDINE; PYRROLIDINE DERIVATIVE; ZIRCONOCENE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; SOLID PHASE SYNTHESIS; STEREOCHEMISTRY;

EID: 33845680676     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951553     Document Type: Article

References (45)

1. (a) Kane, B. E.; Svensson, B.; Ferguson, D. M. AAPS Journal 2006, 8, E126.
2. (b) Glennon, R. A.; Ismaiel, A. M.; Smith, J. D.; Yousif, M.; El-Ashmawy, M.; Herndon, J. L.; Fischer, J. B.; Howie, K. J. B.; Server, A. C. J. Med. Chem. 1991, 34, 1855.
3. Horwell, D. C.; Naylor, D.; Willems, H. M. G. Bioorg. Med. Chem. Lett. 1997, 7, 31.
4. Thomas, C.; Ohnmacht, U.; Niger, M.; Gmeiner, P. Bioorg. Med. Chem. Lett. 1998, 8, 2885.
5. (a) Defauw, J. M.; Murphy, M. M.; Jagdmann, G. E.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R.; Hall, S. E. J. Med. Chem. 1996, 39, 5215.
6. (b) Jagdmann, G. E.; Defauw, J. M.; Lampe, J. W.; Darges, J. W.; Kalter, K. Bioorg. Med Chem. Lett. 1996, 6, 1759.
7. (a) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568.
8. (b) Nugent, W. A.; Taber, D. F. J. Am. Chem. Soc. 1989, 111, 6435.
9. Dixon, S.; Fillery, S. M.; Kasatkin, A.; Norton, D.; Thomas, E.; Whitby, R. J. Tetrahedron 2004, 60, 1401; and references therein.
10. Pyrrolidines: (a) Rousset, C. J.; Swanson, D. R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105.
11. (b) Uesaka, N.; Saitoh, F.; Mori, M.; Shibasaki, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 5633.
12. (c) Saitoh, F.; Mori, M.; Okamura, K.; Date, T. Tetrahedron 1995, 51, 4439.
13. (d) Mori, M.; Kuroda, S.; Zhang, C. S.; Sato, Y. J. Org. Chem. 1997, 62, 3263.
14. (e) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 2000, 3194.
15. Piperidines: (a) Kemp, M. I.; Whitby, R. J.; Coote, S. J. Synthesis 1998, 557.
16. (b) Kemp, M. I.; Whitby, R. J.; Coote, S. J. Synthesis 1998, 552.
17. (c) Mori, M.; Imai, A. E.; Uesaka, N. Heterocycles 1995, 40, 551.
18. (d) Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995, 1237.
19. (e) Azepanes: Macfarlane, D. P. S.; Norton, D.; Whitby, R. J.; Tupper, D. Synlett, submitted.
20. Zhou, Z.-L.; Keana, J. F. W. J. Org. Chem. 1999, 64, 3763.
21. Brown, R. C. D.; Fisher, M. Chem. Commun. 1999, 1547.
22. (a) Bolton, G. L. Tetrahedron Lett. 1996, 37, 3433.
23. (b) Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611.
24. (c) Spitzer, J. L.; Kurth, M. J.; Schore, N. E. Tetrahedron 1997, 53, 6791.
25. Brown, R. C. D.; Castro, J. L.; Moriggi, J. D. Tetrahedron Lett. 2000, 41, 3681.
26. Jones, G. Org. React. 1967, 15, 204.
27. Akamatsu, H.; Kusumoto, S.; Fukase, K. Tetrahedron Lett. 2002, 43, 8867.
28. (a) Yoon, N. M.; Brown, H. C. J. Am. Chem. Soc. 1968, 90, 2927.
29. (b) Matecka, D.; Rothman, R. B.; Radesca, L.; de Costa, B. R.; Dersch, C. M.; Partilla, J. S.; Pert, A.; Glowa, J. R.; Wojnicki, F. H. E.; Rice, K. C. J. Med. Chem. 1996, 39, 4704.
30. (c) Shah, J. H.; Kline, R. H.; Geter-Douglass, B.; Izenwasser, S.; Witkin, J. M.; Newman, A. H. J. Med. Chem. 1996, 39, 3423.
31. (a) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
32. (b) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2929.
33. +] 280.2060; found: 280.2057.
34. (a) Whitesell, J. K.; Minton, M. A. Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy; Chapman and Hall: London, New York, 1987, 37-55.
35. (b) Ando, T.; Kusa, K.; Uchiyama, M.; Yoshida, S.; Takahashi, N. Agric. Biol. Chem. 1983, 47, 2849.
36. 2Zr(1-butene) caused cleavage of the allyl-nitrogen bond rather than cyclisation.
37. Norton, D. PhD Thesis; University of Southampton: UK, 2004.
38. Sasakura, K.; Adachi, M.; Sugasawa, T. Synth. Commun. 1988, 18, 265.
39. Vojkovsky, T. Peptide Res. 1995, 8, 236.
40. 24
41. 2: C, 73.53; H, 8.87; N, 5.36. Found: C, 73.29; H, 8.78; N, 5.40.
42. (a) Bishop, D. C.; Selway, R. A.; Webb, N. E.; Winder, C. V.; Welford, M.; Cavalla, J. F. J. Med. Chem. 1965, 1, 316.
43. (b) Lyles-Eggleston, M.; Altundas, R.; Xia, J.; Sikazwe, D. M. N.; Fan, P.; Yang, Q.; Li, S.; Zhang, W.; Zhu, X.; Schmidt, A. W.; Vanase-Frawley, M.; Shrihkande, A.; Villalobos, A.; Borne, R. F.; Ablordeppey, S. Y. J. Med. Chem. 2004, 47, 497.
44. (c) Sonesson, C.; Wikstrom, H.; Smith, M. W.; Svensson, K.; Carlsson, A.; Waters, N. Bioorg. Med. Chem. Lett. 1997, 7, 241.
45. Leander, D. J.; Cantrell, B. E.; Reel, J. K.; Snoddy, J.; Laurane, M. G.; Johnson, B. G.; Mitch, C. H.; Zimmerman, D. M. J. Med. Chem. 1993, 36, 2833.