Reductive alkylation of aromatic amines with enol ethers

Synlett

Volumn , Issue 4, 2005, Pages 583-586

  Reddy, T Jagadeeswar ^a,b   Leclair, Michael ^a   Proulx, Melanie ^a  

^a ViroChem Pharma Inc   (Canada)

^b MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

2 Methoxypropene; Aromatic amines; Reductive alkylation; Sodium triacetoxyborohydride; Trimethylsilylenol ethers

Indexed keywords

1,2 DICHLOROETHANE; AROMATIC AMINE; ETHER DERIVATIVE; TRIMETHYLSILYL ENOL ETHER; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ROOM TEMPERATURE;

EID: 15444375645     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863704     Document Type: Article

References (24)

1. For reductive amination see review: Hutchins, R. O.; Hutchins, M. K. Comprehensive Organic Synthesis, 1st ed., Vol. 8; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 25-78.
2. (a) Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812.
3. (b) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849; and references cited therein.
4. Apodaca, R.; Xiao, W. Org. Lett. 2001, 3, 1745.
5. 4 or PMHS: (a) see ref.3b
6. (b) Chandrasekhar, S.; Reddy, C. R.; Ahmed, M. Synlett 2000, 1655.
7. (c) Bhattacharya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
8. 14: Park, E. S.; Lee, J. H.; Kim, S. J.; Yoon, C. M. Synth. Commun. 2003, 33, 3387.
9. (a) Chan, L.; Pereira, O.; Reddy, T. J.; Das, S. K.; Poisson, C.; Courchesne, M.; Proulx, M.; Siddiqui, A.; Yannopoulos, C. G.; Nguyen-Ba, N.; Roy, C.; Nasturica, D.; Moinet, C.; Bethell, R.; Hamel, M.; L'Heureux, L.; David, M.; Nicolas, O.; Courtemanche-Asselin, P.; Brunette, S.; Bilimoria, D.; Bédard, J. Bioorg. Med. Chem. Lett. 2004, 14, 797.
10. (b) For preliminary presentation see: Reddy, T. J.; Leclair, M.; Proulx, M.; Quebec and Ontario Mini Symposium in Organic Synthesis November, 2002.
11. (c) There were only two methods available when we carried out our first experiment, see ref. 3.
12. (a) Tapia, I.; Alonso-Cires, L.; Lopez-Tudanca, P. L.; Mosquera, R.; Labeaga, L.; Innerarity, A.; Orjales, A. J. Med. Chem. 1999, 42, 2870.
13. (b) Schaus, J. M.; Thompson, D. C.; Bloomquist, W. E.; Susemichel, A. D.; Calligaro, D. O.; Cohen, M. L. J. Med. Chem. 1998, 41, 1943.
14. For the preparation of N-methylpiperidine enol ether, see: Wanner, K. Liebigs Ann. Chem. 1984, 1103.
15. Few examples of preclinical drugs containing N-isopropyl aromatic amines: (a) HCV NS-3 protease inhibitor, BILN-2061
16. (b) 5-HT-4 receptor antagonists, LY353433
17. (c) 5-HT-4 agonists, BIMU 8.
18. Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. Synthesis 1993, 121.
19. Bhaskar, J. V.; Periasamy, M. J. Org. Chem. 1993, 58, 3156.
20. Couture, A.; Deniau, E.; Gimbert, Y.; Grandclaudon, P. Tetrahedron 1993, 49, 1431.
21. Figge, A.; Altenbach, H. J.; Brauer, D. J.; Tielmann, P. Tetrahedron: Asymmetry 2002, 13, 137.
22. Henke, B. R.; Aquino, C. J.; Birkemo, L. S.; Croom, D. K.; Dougherty, R. W. Jr.; Ervin, G. N.; Grizzle, M. K.; Hirst, G. C.; James, M. K.; Johnson, M. F.; Queen, K. L.; Sherrill, R. G.; Sugg, E. E.; Suh, E. M.; Szewczyk, J. W.; Unwalla, R. J.; Yingling, J.; Willson, T. M. J. Med. Chem. 1997, 40, 2706.
23. Gasc, M. B.; Perie, J.; Lattes, A. Tetrahedron 1978, 34, 1943.
24. Kawakami, T.; Sugimoto, T.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1995, 60, 2677.