Synthesis of a bicyclic piperazine from l-aspartic acid and application of a fluoride-promoted SNAr coupling

Organic Process Research and Development

Volumn 15, Issue 6, 2011, Pages 1328-1335

  Sieser, Janice E ^a   Singer, Robert A ^a   McKinley, Jason D ^a   Bourassa, Dennis E ^a   Teixeira, John J ^a   Long, James ^b  

^a PFIZER INC   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE ROUTES; BOND FORMATION; ISOXAZOLES; L-ASPARTIC ACID; NUCLEOPHILIC AROMATIC SUBSTITUTION; PHASE TRANSFER CATALYSTS; PROCESS DEVELOPMENT;

METHANOL;

AMINO ACIDS;

EID: 81555200726     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op2001854     Document Type: Article

References (39)

1. Salama, I.; Schlotter, K.; Utz, W.; Hubner, H.; Gmeiner, P.; Boeckler, F. Bioorg. Med. Chem. 2006, 14, 5898
2. Peng, H. J. Med. Chem. 2004, 47, 6218
3. Sanner, M. A. Bioorg. Med. Chem. Lett. 1998, 8, 725
4. Bright, G. M.; Desai, K. A. U.S. Patent 5,122,525, 1992
5. Chem. Abstr. 1991, 114, 81886
6. Saleh, M. A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron 1994, 50, 1811
7. Saleh, M. A.; Compernolle, F.; Van den Braden, S.; De Buysser, W.; Hoornaert, G. J. Org. Chem. 1993, 58, 690
8. Compernolle, F.; Saleh, M. A.; Toppet, S.; Hoornaert, G. J. Org. Chem. 1991, 56, 5192
9. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
10. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599
11. Hartwig, J. F.; Shekar, S.; Shen, Q.; Barrios-Landeros, F. In The Chemistry of Anilines; Rappoport, Z., Ed.; Wiley: New York, 2007; p 455.
12. Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000; p 195.
13. NAr. Many heterocycles are intrinsically activated to these pathways as well, see: Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman and Hall: New York, 1995.
14. Some heterocyclic substrates are more challenging to optimize in cross-coupling approaches due to inhibition of the Pd catalyst from the substrate or product. A number of reports have focused on this challenging class of substrates, see: Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 6586
15. Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523
16. Charles, M. D.; Schultz, P.; Buchwald, S. L. Org. Lett. 2005, 7, 3965
17. Yin, J. J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Org. Lett. 2002, 4, 3481
18. Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371
19. Shen, Q.; Ogata, T.; Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861
20. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158
21. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240
22. Aryl chlorides are not as facile to undergo oxidative addition to Pd catalysts as aryl bromides or iodides, especially electron-rich systems, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176
23. Bright, G. M.; Brodney, M. A.; Wlodecki, U.S. Patent 7,345,038 B2, 2008
24. Chem. Abstr. 2004, 141, 296048.
25. Urban, F. J. U.S. Patent 5,719,286 A, 1998
26. Chem. Abstr. 1994, 121, 108844
27. Urban, F. J. J. Heterocycl. Chem. 1995, 32, 857
28. A related route also leading to 17 has been disclosed, see: Urban, F. J.; Breitenbach, R.; Murtishaw, C. W.; Vanderplas, B. V. Tetrahedron: Asymmetry 1995, 6, 321
29. Cyclic secondary amines are known to undergo alkylation with methylene chloride, see: Mills, J. E.; Maryanoff, C. A.; McComsey, D. F.; Stanzione, R. C.; Scott, L. J. Org. Chem. 1987, 52, 1857
30. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505
31. Clark, J. H. Chem. Rev. 1980, 80, 429
32. Yakobson, G. G.; Akhmetova, N. E. Synthesis 1983, 169
33. Fringuelli, F.; Lanari, D.; Pizzo, F.; Vaccaro, L. Curr. Org. Synth. 2009, 6, 203
34. Senanayake, C. H.; Hong, Y.; Xiang, T.; Wilkinson, H. S.; Bakale, R. P.; Jurgens, A. R.; Pippert, M. F.; Butler, H. T.; Wald, S. A. Tetrahedron Lett. 1999, 40, 6875
35. Carpino, L. A.; Sau, A. J. Chem. Soc., Chem. Commun. 1979, 514
36. Leeming, P.; Fronczek, F. R.; Ager, D. J.; Laneman, S. A. Top. Catal. 2000, 13, 175
37. Hubbs, J. C. U.S. Patent 5,144,073 A, 1992
38. Toshihisa, K.; Tadashi, T. Eur. Pat. Appl. EP 493812, 1992.
39. 3 for improving the efficiency of the conversion to the chloride has been reported previously, see: Andersen, K.; Begtrup, M. Acta Chem. Scand. 1992, 46, 1130