Stereoselective preparation of a cyclopentane-based NK1 receptor antagonist bearing an unsymmetrically substituted sec-sec ether

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7378-7390

  Kuethe, Jeffrey T ^a   Marcoux, Jean Francois ^a   Wong, Audrey ^a   Wu, Jimmy ^a   Hillier, Michael C ^a   Dormer, Peter G ^a   Davies, Ian W ^a   Hughes, David L ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL REACTIONS; CRYSTALLIZATION; ETHERS; MIXTURES; SYNTHESIS (CHEMICAL);

DIASTEREOMERS; DIASTEREOSELECTIVITY; ETHERIFICATION; TRIETHYLAMINE SOLVATE 44;

STEREOCHEMISTRY;

BORON DERIVATIVE; CYCLOPENTANE DERIVATIVE; ETHER DERIVATIVE; FLUORINE DERIVATIVE; IMIDE; NEUROKININ 1 RECEPTOR ANTAGONIST; TRIETHYLAMINE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHIRALITY; CRYSTALLIZATION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ETHERIFICATION; ISOLATION PROCEDURE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

CYCLOPENTANES; ETHERS; MOLECULAR STRUCTURE; RECEPTORS, NEUROKININ-1;

EID: 33749017612     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061268x     Document Type: Article

References (70)

1. (a) Quatara, L.; Maggi, C. A. Neuropeptides 1998, 32, 1.
2. (b) Rupniak, N. M. J.; Kramer, M. S. Trends Pharmacol. Sci. 1999, 20, 485.
3. (c) Seward, E. M.; Swain, C. J. Expert Opin. Ther. Pat. 1999, 9, 571.
4. (d) Kramer, M. S.; Cutler, N.; Feighner, J.; Shrivastava, R.; Carman, J.; Sramek, J. J.; Reins, S. A.; Liu, G.; Snavely, D.; Wyatt-Knowles, E.; Hale, J. J.; Mills, S. G.; MacCoss, M.; Swain, C. J.; Harrison, T.; Hill, R. G.; Hefti, F.; Scolnick, E. M.; Cascieri, M. A.; Chicchi, G. G.; Sadowski, S.; Williams, A. R.; Hewson, L.; Smith, D.; Carlson, E. J.; Hargreaves, R. J.; Rupniak, N. M. J. Science 1998, 281, 1640.
5. (e) Snider, R. M.; Constantine, J. W.; Lowe, J. A., III; Longo, K. P.; Lebel, W. S.; Woody, H. A.; Drozda, S. E.; Desari, M. C.; Vinick, F. J.; Spencer, R. W.; Hess, H.-J. Science 1991, 251, 435.
6. (a) Regoli, D.; Boudon, A.; Fauchere, J.-L. Pharmacol. Rev. 1994, 46, 551.
7. (b) Swain, C. J. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Oxford, A. W., Eds.; Elsevier Science BV: Amsterdam, 1998; Vol. 35, pp 57-81.
8. (c) Harrison, T.; Williams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545.
9. (d) Shaw, D.; Chicchi, G. G.; Elliott, J. M.; Kurtz, M. M.; Morrison, D.; Ridgill, M. P.; Szeto, N.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 3031.
10. (e) Elliot, J. M.; Castro, J. L.; Chicchi, G. G.; Cooper, L. C.; Dinnell, K.; Hollingworth, G. J.; Ridgill, M. P.; Rycroft, W.; Kurtz, M. M.; Shaw, D. E.; Swain, C. J.; Tsao, K.-L.; Yang, L. Bioorg. Med. Chem. Lett. 2002, 12, 1755.
11. (f) Cooper, L. C.; Carlson, E. J.; Castro, J. L.; Chicchi, G. G.; Dinnell, K.; Di Salvo, J.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Ridgill, M. P.; Rycroft, W.; Tsao, K.-L.; Swain, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 1759.
12. (g) Seward, E. M.; Carlson, E.; Harrison, T.; Haworth, K. E.; Herbert, R.; Kelleher, F. J.; Kurtz, M. M.; Moseley, J.; Owen, S. N.; Owens, A. P.; Sadowski, S. J.; Swain, C. J.; Williams, B. J. Bioorg. Med. Chem. Lett. 2002, 12, 2515.
13. (h) Williams, B. J.; Cascieri, M. A.; Chicchi, G. G.; Harrison, T.; Owens, A. P.; Owens, S. N.; Rupniak, N. M. J.; Tattersall, F. D.; Williams, A.; Swain, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 2719.
14. (i) Gale, J. D.; O'Neill, B. T.; Humphrey, J. M. Expert Opin. Ther. Pat. 2001, 11, 1837.
15. (a) Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. Bioorg. Med. Chem. Lett. 2005, 15, 1485.
16. (b) Ishichi, Y.; Ikeura, Y.; Natsugari, H. Tetrahedron 2004, 60, 4481.
17. (c) Albert, J. S.; Ohnmacht, C.; Bernstein, P. R.; Rumsey, W. L.; Aharony, D.; Alelyunas, T.; Russell, D. J.; Potts, W.; Sherwood, S. A.; Shen, L.; Dedians, R. F.; Palmer, W. E.; Russel, K. J. Med. Chem. 2004, 47, 519.
18. (d) Reichard, G. A.; Stengone, C.; Paliwal, S.; Mergelsberg, I.; Majmundar, S.; Wang, C.; Tiberi, R.; McPhail, A. T.; Piwinski, J. J.; Shih, N.-Y. Org. Lett. 2003, 5, 4249.
19. Hale, J. J.; Mills, S. G.; MacCoss, M.; Finke, P. E.; Cascieri, M. A.; Sadowski, S.; Ber, E.; Chicchi, G. C.; Kurtz, M.; Metzger, J.; Eiermann, G.; Tsou, N. N.; Tattersall, F. D.; Rupniak, N. M. J.; Williams, A. R.; Rycroft, W.; Hargreaves, R.; MacIntyre, D. E. J. Med. Chem. 1998, 41, 4607.
20. (a) Brands, K. M. J.; Payack, J. F.; Rosen, J. D.; Nelson, T. D.; Candelario, A.; Huffman, M. A.; Zhao, M. M.; Li, J.; Craig, B.; Song, Z. J.; Tschaen, D. M.; Hansen, K.; Devine, P. N.; Pye, P. J.; Rossen, K.; Dormer, P. G.; Reamer, R. A.; Welch, C. J.; Mathre, D. J.; Tsou, N. N.; McNamara, J. M.; Reider, P. J. J. Am. Chem. Soc. 2002, 125, 2129.
21. (b) Zhao, M. M.; McNamara, J. M.; Ho, G.-J.; Emerson, K. M.; Song, Z. J.; Tschaen, D. M.; Brands, K. M. J.; Dolling, U.-H.; Grabowski, E. J. J.; Reider, P. J.; Cotrell, I. F.; Ashwood, M. S.; Bishop, B. C. J. Org. Chem. 2002, 67, 6743.
22. (c) Pye, P. J.; Rossen, K.; Weissman, S. A.; Maliakal, A.; Reamer, R. A.; Ball, R.; Tsou, N. N.; Volante, R. P.; Reider, P. J. Chem. Eur. J. 2002, 8, 1372.
23. (a) Finke, P. E.; Meurer, L.; MacCoss, M.; Mills, S. G.; Sadowski, S.; Cascieri, M. A.; Metzger, J.; Eiermann, G.; MacIntyre, D. E. Presented at the 219th National Meeting of the American Chemical Society, San Francisco, CA, March 2000; Abstract 98.
24. (b) Meurer, L.; Finke, P. E.; MacCoss, M.; Mills, S. G.; Tsou, N.; Ball, R. G.; Sadowski, S.; Cascieri, M. A.; Metzger, J.; Eiermann, B.; MacIntyre, D. E.; Rupniak, N. M. J.; Williams, A. Presented at the 219th National Meeting of the American Chemical Society, San Francisco, CA, March 2000; Abstract 99.
25. (c) Finke, P. E. Presented at the National Medicinal Chemistry Symposium, Madison, WI, June 2004.
26. (d) Finke, P. E.; Meurer, L. C.; Levorse, D. A.; Mills, S. G.; MacCoss, M.; Sadowski, S.; Cascieri, M. A.; Tsao, K.-L.; Chicchi, G. G.; Metzger, J. M.; MacIntyre, D. E.; Bioorg. Med. Chem. Lett. 2006, 16, 4497.
27. (e) Meurer, L. C.; Finke, P. E.; Levorse, D. A.; Mills, S. G.; MacCoss, M.; Tsou, N.; Ball, R. G.; Sadowski, S.; Cascieri, M. A.; Chicchi, G. G.; Egger, L. A.; Luell, S.; Metzger, J. M.; MacIntyre, D. E.; Rupniak, N. M. J.; Williams, A. R.; Hargreaves, R. J. Bioorg. Med. Chem. Lett. 2006, 16, 4504.
28. (f) Desai, R. C.; Cicala, P.; Meurer, L. C.; Finke, P. E. Tetrahedron Lett. 2002, 43, 4569.
29. (a) Caldwell, C. G.; Chen, P.; Durette, P. L.; Finke, P.; Hale, J.; Holson, E.; Kopka, I.; MacCoss, M.; Meurer, L.; Mills, S. G.; Robichaud, A. U.S. Patent 5,750, 549, 1998.
30. (b) Finke, P. E.; Meurer, L. C.; Qi, H.; Mills, S. G.; MacCoss, M. U.S. Patent 6,479, 518, 2002.
31. Kuethe, J. T.; Wong, A.; Wu, J.; Davies, I. W.; Dormer, P. G.; Welch, C. J.; Hillier, M. C.; Hughes, D. L.; Reider, P. J. J. Org. Chem. 2002, 67, 5993.
32. For an extensive list of ether forming reactions, see: Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 881-958.
33. (a) Kim, H.; Lee, C. Org. Lett. 2002, 4, 4369.
34. (b) Roberts, J. P.; Lee, C. Org. Lett. 2005, 7, 2679.
35. For leading references, see: (a) Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473.
36. (b) Crimmins, M. T.; She, J. Synlett 2004, 1371.
37. (c) Crimmins, M. T.; Ellis, J. M. J. Am. Chem. Soc. 2005, 127, 17200.
38. Rychnovsky, S. D.; Cossrow, J. Org. Lett. 2003, 5, 2367.
39. Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 1998, 9, 1771 and references therein.
40. (a) Narkevitch, V.; Schenk, K.; Vogel, P. Angew. Chem., Int. Ed. 2000, 39, 1806.
41. (b) Narkevitch, V.; Megevand, S.; Schenk, K.; Vogel, P. J. Org. Chem. 2001, 66, 5080.
42. For leading references on diastereoselective hydrogenations, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
43. (b) Bouzide, A. Org. Lett. 2002, 4, 1347.
44. (c) Ikemoto, N.; Tellers, D. M.; Dreher, S. D.; Liu, J.; Huang, A.; Rivera, N. R.; Njolito, E.; Hsiao, Y.; McWilliams, J. C.; Williams, J. M.; Armstrong, J. D., III; Sun, Y.; Mathre, D. J.; Grabowski, E. J. J.; Tillyer, R. D. J. Am. Chem. Soc. 2004, 126, 3048 and references therein.
45. Payack, J. F.; Huffman, M. A.; Cai, D.; Hughes, D. L.; Collins, P. C.; Johnson, B. K.; Cottrell, I. F.; Tuma, L. D. Org. Process Res. Dev. 2004, 8, 256 and references therein.
46. (a) Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367.
47. (b) Sassaman, M. B.; Kotian, K. D.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1987, 52, 4314.
48. (c) Komatsu, N.; Ishida, J.; Suzuki, H. Tetrahedron Lett. 1997, 38, 7219.
49. (d) Kato, J.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1985, 743.
50. (a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 20, 4679.
51. (b) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
52. HPLC assay yield refers to quantitative HPLC analysis of the crude reaction mixtures using an analytically pure standard.
53. The Titan software package was used to perform the analysis. The "Conformer Study" option was selected as a computation type, and PM3 was selected as the method, the results in conformations being generated using the included MMFF94 molecular mechanics force field and the resulting structures being minimized with the PM3 semiempirical method. Calculations were performed in the gas phase.
54. The following Z conformations were ∼3 kcal/mol higher in energy and most likely do not contribute to the stereochemical outcome of the reaction: (Diagram presented)
55. For leading references, see: (a) Iversen, T.; Bundle, D. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
56. (b) Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 731.
57. (c) Schmidt, R. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1983, 22, 406.
58. (d) Wessel, H. P.; Iversen, T.; Bundel, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
59. (e) Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
60. (f) Nakajima, N.; Saito, M.; Ubukata, M. Tetrahedron Lett. 1998, 39, 5565.
61. (g) Eichler, E.; Yan, F.; Sealy, J.; Whitfield, D. M. Tetrahedron 2001, 57, 6679.
62. (h) Kusumoto, T.; Hanamoto, T.; Sato, K.; Hiyama, T.; Takehara, T.; Shoji, T.; Osawa, M.; Kuiyama, T.; Nakamura, K.; Fujisawa, T. Tetrahedron Lett. 1990, 31, 5343.
63. Available from Aldrich Chemical Co.
64. Commercially available 54 wt % tetrafluoroboric acid solution in diethyl ether was used in all transformations.
65. The individual components of the crude reaction mixture were identified by analysis of the crude NMR and were not separated from one another.
66. We cannot completely rule out a matched-mismatched interaction between chiral alcohol 4 and imidates 30 and 31.
67. Carpenter, B. K. Determination of Organic Reaction Mechanisms; John Wiley and Sons: New York, 1984.
68. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds; Springer-Verlag: New York, 1978.
69. Das, J.; Kimball, S. D.; Reid, J. A.; Wang, T. C.; Lau, W. F.; Roberts, D. G. M.; Seiler, S. M.; Schumacher, W. A.; Ogletree, M. L. Bioorg. Med. Chem. Lett. 2002, 12, 41.
70. Grigan, N.; Musel, D.; Veinberg, G. A.; Lukevics, E. Synth. Commun. 1996, 26, 1183.