Kilogram synthesis of a selective serotonin reuptake inhibitor

Organic Process Research and Development

Volumn 12, Issue 2, 2008, Pages 168-177

  Anthes, Robert ^a   Bello, Osagie ^a   Benoit, Serge ^a   Chen, Chien Kuang ^a   Corbett, Elisabeth ^a   Corbett, Richard M ^a   DelMonte, Albert J ^a   Gingras, Stephane ^a   Livingston, Robert ^a   Sausker, Justin ^a   Soumeillant, Maxime ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149171592     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op700125z     Document Type: Article

References (54)

1. (a) Nagatomo, T.; Rashid, M.; Muntasir, H. A.; Komiyama, T. Pharmacol. Ther. 2004, 104, 59.
2. (b) Middlemiss, D. N.; Price, G. W.; Watson, J. M. Curr. Opin. Pharmacol. 2002, 2, 18.
3. (a) Currently available drugs in this class include Citalopram, Escitalopram, Fluoxetine, Fluvoxamine, Paroxetine, and Sertraline. Malinin, A.; Oshrine, B.; Serebruany, V. Med. Hypothesis 2004. 63, 103.
4. (b) Chen, J.; Mabjeesh, H.; Greenstein, A. Urology 2003, 61, 197.
5. (c) Dimmock, P. W.; Wyatt, K. M.; Jones. P. W.; Shaughn O'Brien, P. M. Lancet 2000, 356, 1131.
6. (d) Moore, K. Int. J. Gynecol. Obstet. 2004, 86 (1), S53.
7. (e) Pogarell, O.; Poepperl, G.; Muiert. C.; Hamann, C.; Sadowsky, N.; Riedel, M.; Moeller, H.-J.; Hegerl, U.; Tatsch, K Eur. Neuropsychopharmacol. 2005, 15, 521-524.
8. (a) King. H.; DMeng. Z.: Denhart. D.; Mattson, R.; Kimura. R.; Dedong, W.; Gao, Q.; Macor, J. E Org. Lett. 2005. 7, 3437.
9. (b) Taylor, E. W.; Nikam, S.; Week, B.; Martin, A.; Nelson, D. Life Sci. 1987, 41, 1961.
10. (c) Vangveravong, S.; Kanthasamy, A.; Lucaites, V. L.; Nelson, D. L.: Nichols, D. E. J. Med. Chem. 1998, 41, 4995.
11. (d) Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor. A.; Alvarez, P.; Vaquero, J. J. Tetrahedron Lett. 1996, 37, 683.
12. (e) Macor, J. E.; Blank, D. H.; Post, R. J. Tetrahedron Lett. 1994, 35, 45.
13. (f) Macor, J. E.; Blank, D. H.; Ryan, K.; Post, R. J. Synthesis 1997, 443.
14. (g) Schmitz, W. D.; Denhart, D. J.; Brenner, A. B.; Ditta, J. L.; Mattson, R. J.; Mattson, G. K.; Molski, T. F.; Macor, J. E. Bioorg. Med. Chem. Lett. 2005, 15, 1619.
15. (h) Mattson, R. J.; Catt, J. D.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Higgins, M. A.; Marcin, L. R.; Sloan, C. P.; Beno, B. R.; Gao, Q.; Cunningham, M. A.; Mattson, G. K.; Molski, T. F.; Taber, M. T.; Lodge, N. J. J. Med. Chem. 2005, 48, 6023.
16. (a) Mattson, R. J.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Marcin, L. R.; Epperson, J. R.; Catt, J. D.; King, D.; Higgins, M. A. (Bristol- Myers Squibb) Cyclopropylindole derivatives as selective serotonin reuptake inhibitors, U.S. patent US6777437 B2, Aug 17, 2004.
17. (b) Mattson, R. J. (Bristol-Myers Squibb) Cyclopropylindole derivatives as selective serotonin reuptake inhibitors, U.S. patent US6822100 B2, Nov 23, 2004.
18. (c) Mattson, R. J.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Marcin, L. R.; Epperson, J. R.; Catt, J. D.; King, D.; Higgins, M. A. (Bristol-Myers Squibb) Cyclopropylindole derivatives as selective serotonin reuptake inhibitors, PCT Int. Appl. WO 0279152, 2002.
19. Similar disconnection was employed during multi-kilogram scale preparation of a melatonin antagonist. Simpson, J. H.; Godfrey, J.; Fox, R.; Kotnis, A.; Kacsur, D. J.; Hamm, J,; Totleben, M.; Rosso, V.; Mueller, R.; Delaney, E.; Deshpande, R. P. Tetrahedron Asymmetry 2003, 14, 3569.
20. Marcin, L. R.; Denhart, D. J.; Mattson, R. J. Org. Lett. 2005, 7, 2651.
21. The Drug Discovery conversion of aldehyde 5 to vinyl indole 2 involved Wittig olefination. Although the Wittig chemistry was effective, two-step methyl Grignard addition followed by dehydration was found to be operationally simpler.
22. mL/g refers to milliliters of solvent per grams of substrate.
23. Sundberg, R. J.; Amat, M.; Fernando, A. M. J. On;. Chem. 1987, 52 (14), 3151.
24. A 4 min HPLC method was developed to minimize exposure of the product to the reaction conditions.
25. (a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B. J. Am. Chem, Soc. 1994, 116, 2223.
26. (b) Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron Asymmetry 1995, 6, 2487.
27. (c) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
28. (d) Totleben, M. J.; Prasad, J. S.; Simpson, J. H.; Chan, S. H.; Vanyo, D. J.; Kuehner, D. E.; Deshpande, R.; Kodersha, G. A. J. Org. Chem. 2001, 66, 1057.
29. (a) Subsequent to the work described here, significant advances in the field of cyclopropanation chemistry were reported by many research groups. For representative examples, see: Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B Chem. Rev. 2003, 103, 977.
30. (b) Liao, W.-W.; Li, K.; Tang. Y J. Am. Chem. Soc. 2003. 125, 13030.
31. (c) Long, J.; Yuan, Y.; Shi, Y. J. Am. Chem. Soc. 2003, 125, 13632.
32. (d) Aggarwal, V. K.; Fang, G. Y.; Meek, G. Org. Lett. 2003, 5, 4417.
33. (e) Risatti, C. A.; Taylor, R. E. Angew. Chem., Int. Ed. 2004. 43, 6671.
34. (f) Moreau, B.; Charette, A. J. Am. Chem. Soc. 2005, 127, 18014.
35. (g) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
36. (h) Bykowski, B.; Wu, K.-H.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 16038.
37. (i) Thompson, J. L.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 6090.
38. (j) Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am, Chem. Soc. 2007, 129, 10886.
39. (a) Kotnis, A. S.; Simpson, J. H.; Deshpande, R. P.; Kacsur, D. J.; Hamm, J.; Kodersha, G.; Merkl,W.; Domina, D.; Wang, S. S. Y. Manuscript in preparation.
40. (b) Clark, J. D.; Shah, A. S.; Peterson, J. C.; Patelis, L.; Kersten, R. J.; Heemskerk, A. H. Thermochim. Acta 2002, 386, 73.
41. (c) Clark, J. D.; Shah, A. S.; Peterson, J. C.; Patelis, L.; Kersten, R. J.; Heemskerk, A. H.; Grogan, M.; Camden, S. Thermochim. Acta 2002, 386, 65.
42. (d) Armstrong, R. K. J. Org. Chem. 1996, 31, 618.
43. (e) Searle, N. E. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 424.
44. (f) DelMonte, A. J.; Dowdy, E. D.; Watson, D. J. Development of Transition Metal-Mediated Cyclopropanation Reactions. In Topics in Organometallic Chemistry; Larsen, R. D., Ed.; Springer: Berlin, New York, 2004; Vol. 6, Organometallics in Process Chemistry; pp 97-122.
45. 2 (reflux), 92.4% ee with 13.1:1 trans:cis ratio and 56.5% conversion; in MTBE (50 °C), 87.6% ee with 12.9:1 trans:cis ratio and >99% conversion; in methylisobutylketone (50 °C), 86.3% ee with 14.7:1 trans:cis ratio and 82.7% conversion; in butylacetate (50 °C), 85.6% ee with 11.6:1 trans:cis ratio and 98.7% conversion; in triflurotouluene (50 °C), 86.3% ee (trans:cis ratio ND) and 67.9% conversion; in acetonitrile no conversion was achieved, most likely due to complexation of acetonitrile with ruthenium (See: Cadiemo, V.; Gamasa, M. P.; Gimeno, J.; Inglesias, L.; Garcia-Granda, S. Inorg. Chem. 1999, 38, 2874.
46. Clark, J. D.; Shah, A. S.; Peterson, J. C. Thermochim. Acta 2002, 177, 392-393.
47. Chen, C.-K.; Singh, A. A. Org. Process Res. Dev. 2001, 5, 508.
48. For a detailed analysis of a similar system see: Org. Process Res. Dev. 2004, 6, 1072-1075.
49. Chem. Eng. News 2002, 80, 7.
50. (a) Anelli, P. L.; Biffi, F. M.; Quici, S. J. Org. Chem. 1987, 52, 2559.
51. (b) de Nooy, A. E, J.; Besemer, A. C.; van Bekkum, H, Tetrahedron 1995, 51, 8023.
52. Jeffery, G. H.; Bassett, J.; Mendham, J.; Denney, R. C. Vogel's Textbook of Quantitative Chemical Analysis, 5th ed.; Prentice Hall: Singapore,' 1989; pp 396-397..
53. http://www.cuno.com/labstore/dfs-zetacarbon.shtml.
54. http://www.jmcatalysts.com/pct/marketshome.asp?marketid=69&id= 250.