First direct reductive amination of mucochloric acid: A simple and efficient method for preparing highly functionalized α,β-unsaturated γ-butyrolactams

Organic Letters

Volumn 5, Issue 4, 2003, Pages 553-556

  Zhang, Ji ^a   Blazecka, Peter G ^a   Davidson, James G ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; ACID; ANTIDEPRESSANT AGENT; BENZYLAMINE DERIVATIVE; KETONE DERIVATIVE; LACTAM DERIVATIVE; MUCOCHLORIC ACID; ROLICYPRINE; ROLIPRAM; UNCLASSIFIED DRUG; BETA LACTAM; FURAN DERIVATIVE; PYRROLIDINE DERIVATIVE;

AMINATION; ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; DRUG MECHANISM; INHIBITION KINETICS; NEUROTRANSMISSION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; CHEMISTRY; DRUG DESIGN; SYNTHESIS;

AMINATION; BETA-LACTAMS; DRUG DESIGN; FURANS; GAMMA-AMINOBUTYRIC ACID; PYRROLIDINES;

EID: 0037561145     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0274662     Document Type: Article

References (76)

1. (a) Corey, E. J.; Li, W.-D. Chem. Pharm. Bull. 1999, 47, 1.
2. (b) Baldwin, J. E.; Lynch, G. P.; Pitlik, J. J. Antibiot. 1991, 44, 1.
3. (a) Yee, N. K.; Dong, Y.; Kapadia, S. R.; Song, J. J. J. Org. Chem. 2002, 67, 8688.
4. (b) Xie, X.; Lu, X.; Liu, Y.; Xu, W. J. Org. Chem. 2001, 66, 6545.
5. Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Old, D. W.; Mooney, P. A. J. Org. Chem. 1996, 61, 5813.
6. Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217.
7. Duan, J. J.-W.; Chen, L.; Wasserman, Z. R.; Lu, Z.; Liu, R.-Q.; Covington, M. B.; Qian, M.; Hardman, K. D.; Magolda, R. L.; Newton, R. C.; Christ, D. D.; Wexler, R. R.; Decicco, C. P. J. Med. Chem. 2002, 45, 4954.
8. (a) Fu, M.; Nikolic, D.; Van Breemen, R. B.; Silverman, R. B. J. Am. Chem. Soc. 1999, 121, 7751.
9. (b) Silverman, R. B.; Bichler, K. A.; Leon, A. J. J. Am. Chem. Soc. 1996, 118, 1253.
10. (c) Silverman, R. B.; Bichler, K. A.; Leon, A. J. J. Am. Chem. Soc. 1996, 118, 1241.
11. (a) Warner-Lambert; Neurontin (gabapentin). U.S. Patent 4,024,175, 1977.
12. (b) Doyle, M. P.; Hu, W. Chirality 2002, 14, 169. Carpes, M. J. S.; Correia, C. R. D. Tetrahedron Lett. 2002, 43, 741. Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.
13. (b) Doyle, M. P.; Hu, W. Chirality 2002, 14, 169. Carpes, M. J. S.; Correia, C. R. D. Tetrahedron Lett. 2002, 43, 741. Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.
14. (b) Doyle, M. P.; Hu, W. Chirality 2002, 14, 169. Carpes, M. J. S.; Correia, C. R. D. Tetrahedron Lett. 2002, 43, 741. Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.
15. (c) Hoekstra, M. S.; Sobieray, D. M.; Schwindt, M. A.; Mulhern, T. A.; Grote, T. M.; Huckabee, B. K.; Hendrickson, V. S.; Franklin, L. C.; Granger, E. J.; Karrick, G. L. Org. Process Res. Dev. 1997, 1, 26.
16. (a) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
17. (b) Barnes, D. M.; Ji, J.; Fickes, M. G.; Fitzgerald, M. A.; King, S. A. ; Morton, H. E.; Plagge, F. A.; Preskill, M.; Wagaw, S. H.; Wittenberger, S. J. ; Zhang, J. J. Am. Chem. Soc. 2002, 124, 13097.
18. (c) Anada, M.; Mita, O.; Watanabe, H.; Kitagaki, S.; Hashimoto, S. Synlett 1999, 1775.
19. (d) Diaz, A.; Siro, J. G.; Garcia-Navio, J. L.; Vaquero, J. J.; Alvarez-Builla, J. Synthesis 1997, 559.
20. (e) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36.
21. (f) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl., 1992, 31, 870.
22. (g) Goldenthal, E. I. Toxicol. Appl. Pharmacol. 1971, 18, 185.
23. Denis, J.-N.; Tchertchian, S.; Tomassini, A.; Vallee, Y. Tetrahedron Lett. 1997, 38, 5503.
24. (a) Dixon, D. J.; Ley, S. V.; Rodriguez, F. Org. Lett. 2001, 3, 3753.
25. (b) Forti, L.; Ghelfi, F.; Levizzani, S.; Pagnoni, U. M. Tetrahedron Lett. 1999, 40, 3233.
26. (c) Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1997, 8, 133.
27. (d) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210.
28. (e) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
29. (f) Wei, Z.-Y.; Knaus, E. E. Tetrahedron 1994, 50, 5569.
30. Collins, C. J.; Lanz, M.; Singaram, B. Tetrahedron Lett. 1999, 40, 3673 and references therein.
31. Nagai, Y.; Uno, H.; Umemoto, S. Chem. Pharm. Bull. 1977, 25, 1911.
32. (a) Ma, Z.; Chu, D. T. W.; Cooper, C. S.; Li, Q.; Fung, A. K. L.; Wang, S.; Shen, L. L.; Flamm, R. K.; Nilius, A. M.; Alder, J. D.; Meulbroek, J. A.; Or, Y. S. J. Med. Chem. 1999, 42, 4202.
33. (b) Hong, C. Y.; Kim, Y. K.; Chang, J. H.; Kim, S. H.; Choi, H.; Nam, D. H.; Kim, Y. Z.; Kwak, J. H. J. Med. Chem. 1997, 40, 3584.
34. (a) Hanessian, S.; Claridge, S.; Johnstone, S. J. Org. Chem. 2002, 67, 4261.
35. (b) Das, J.; Floyd, D. M.; Kimball, S. D.; Duff, K. J.; Lago, M. W.; Krapcho, J.; White, R. E.; Ridgewell, R. E.; Obermeier, M. T.; et al. J. Med. Chem. 1992, 35, 2610.
36. (a) Lee, D.; Long, S. A.; Murray, J. H.; Adams, J. L.; Nuttall, M. E.; Nadeau, D. P.; Kikly, K.; Winkler, J. D.; Sung, C.-M.; Ryan, M. D.; Levy, M. A. ; Keller, P. M.; DeWolf, W. E., Jr. J. Med. Chem. 2001, 44, 2015.
37. (b) Chang, A.-C.; Cowan, A.; Takemori, A. E.; Portoghese, P. S. J. Med. Chem. 1996, 39, 4478.
38. (a) Andrews, D. M.; Chaignot, H.; Coomber, B. A.; Good, A. C.; Hind, S. L.; Johnson, M. R.; Jones, P. S.; Mills, G.; Robinson, J. E.; Skarzynski, T.; Slater, M. J.; Somers, D. O. Org. Lett. 2002, 4, 4479.
39. (b) Andrews, D. M.; Carey, S. J.; Chaignot, H.; Coomber, B. A.; Gray, N. M.; Hind, S. L.; Jones, P. S.; Mills, G.; Robinson, J. E.; Slater, M. J. Org. Lett. 2002, 4, 4475.
40. (a) Vecchietti, V.; Clarke, G. D.; Colle, R.; Dondio, G.; Giardina, G.; Petrone, G.; Sbacchi, M. J. Med. Chem. 1992, 35, 2970.
41. (b) Vecchietti, V.; Clarke, G. D.; Colle, R.; Giardina, G.; Petrone, G.; Sbacchi, M. J. Med. Chem. 1991, 34, 2624.
42. Flaniken, J. M.; Collins, C. J.; Lanz, M.; Singaram, B. Org. Lett. 1999, 1, 799.
43. Chatani, N.; Kamitani, A.; Murai, S. J. Org. Chem. 2002, 67, 7014.
44. Zhang, J.; Blazecka, P. G.; Belmont, D.; Davidson, J. G. Org. Lett. 2002, 4, 4559.
45. (a) Koenig, H. Angew. Chem. GE 1980, 92, 802.
46. (b) Bistrzycki, H. Chem. Ber. 1901, 34, 1014.
47. (a) Bandini, E.; Martelli, G.; Spunta, G.; Bongini, A.; Panunzio, M.; Piersanti, G. Tetrahedron: Asymmetry 1999, 10, 1445.
48. (b) Giambastiani, G.; Pacini, B.; Porcelloni, M.; Poli, G. J. Org. Chem. 1998, 63, 804 and references therein.
49. (a) Yoon, C. H.; Zaworotko, M. J.; Moulton, B.; Jung, K. W. Org. Lett. 2001, 3, 3539 and references therein.
50. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 5629.
51. (c) Chatterjee, B. G.; Sahu, D. P. J. Org. Chem. 1977, 42, 3162.
52. (d) Giering, W. P.; Raghu, S.; Rosenblum, M.; Cutler, A.; Ehtholt, D.; Fish, R. W. J. Am. Chem. 1972, 94, 8251.
53. (a) Dieter, R. K.; Lu, K.; J. Org. Chem. 2002, 67, 847.
54. (b) Dieter, R. K.; Lu, K. Tetrahedron Lett. 1999, 40, 4011.
55. (c) Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. J. Org. Chem. 1999, 64, 1979.
56. (d) Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. Tetrahedron Lett. 1998, 39, 1698.
57. (e) Pearson, W, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669.
58. (f) Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
59. (g) Larock, R. C.; Yang, H.; Weinreb, S. M.; Herr, R. J. J. Org. Chem. 1994, 59, 4172.
60. (h) Zhou, J. Q.; Alper, H. J. Org. Chem. 1992, 57, 3328.
61. (i) Padwa, A.; Nimmesgem, H.; Wong, G. S. K. Tetrahedron Lett. 1985, 26, 957.
62. (j) Overman, L. E.; Kakimoto, M.; Okazaki, M. E.; Meier, G. P. J. Am. Chem. Soc. 1983, 105, 6622.
63. (k) Padwa, A.; Chen, Y. Y. Tetrahedron Lett. 1983, 24, 3447.
64. (a) Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
65. (b) Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595.
66. For another method of preparing N-aryl heterocycles, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
67. For another method of preparing N-aryl heterocycles, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
68. th ed.; Merck & Co., Inc.: Whitehouse, NJ, 1996; p 1079. (b) 2003-2004 Aldrich Handbook of Fine Chemicals and Laboratory Equipment; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; p 1313. (c) Acros Organics 2002/03 Catalog of Organics and Fine Chemicals; Fisher Scientific Company, L.L.C.: Pittsburgh, PA, 2002; p 1523. (d) Lancaster 2002-3 Research Chemicals Catalog; Lancaster Synthesis, Inc.: Windham, NH, 2002; p 1304.
69. th ed.; Merck & Co., Inc.: Whitehouse, NJ, 1996; p 1079. (b) 2003-2004 Aldrich Handbook of Fine Chemicals and Laboratory Equipment; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; p 1313. (c) Acros Organics 2002/03 Catalog of Organics and Fine Chemicals; Fisher Scientific Company, L.L.C.: Pittsburgh, PA, 2002; p 1523. (d) Lancaster 2002-3 Research Chemicals Catalog; Lancaster Synthesis, Inc.: Windham, NH, 2002; p 1304.
70. th ed.; Merck & Co., Inc.: Whitehouse, NJ, 1996; p 1079. (b) 2003-2004 Aldrich Handbook of Fine Chemicals and Laboratory Equipment; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; p 1313. (c) Acros Organics 2002/03 Catalog of Organics and Fine Chemicals; Fisher Scientific Company, L.L.C.: Pittsburgh, PA, 2002; p 1523. (d) Lancaster 2002-3 Research Chemicals Catalog; Lancaster Synthesis, Inc.: Windham, NH, 2002; p 1304.
71. th ed.; Merck & Co., Inc.: Whitehouse, NJ, 1996; p 1079. (b) 2003-2004 Aldrich Handbook of Fine Chemicals and Laboratory Equipment; Aldrich Chemical Co., Inc.: Milwaukee, WI, 2003; p 1313. (c) Acros Organics 2002/03 Catalog of Organics and Fine Chemicals; Fisher Scientific Company, L.L.C.: Pittsburgh, PA, 2002; p 1523. (d) Lancaster 2002-3 Research Chemicals Catalog; Lancaster Synthesis, Inc.: Windham, NH, 2002; p 1304.
72. (a) Wasserman, H. H.; Precopio, F. M. J. Am. Chem. Soc. 1952, 74, 326. (b) Mowry, D. T. J. Am. Chem. Soc. 1950, 72, 2535.
73. (b) Mowry, D. T. J. Am. Chem. Soc. 1950, 72, 2535.
74. Moore, R. D.; Katon, J. E. Appl. Spectrosc. 1978, 32, 145.
75. Valente, E. J.; Fuller, J. F.; Ball, J. D. Acta Crystallogr., Sect. B. Struct. Sci. 1998, B54, 162.
76. Mucobromic acid (2) gave the corresponding bromides when subjected to similar reaction conditions. Unpublished results.