An orthogonal protection strategy for the synthesis of 2-substituted piperazines

Tetrahedron

Volumn 63, Issue 14, 2007, Pages 3057-3065

  Clark, Roger B ^a   Elbaum, Daniel ^a  

^a Critical Therapeutics Inc   (United States)

Author keywords

2 (Phenoxymethyl)piperazines; Orthogonal protection; Oxazolidinone; Piperazine

Indexed keywords

BENZYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; OXAZOLE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; OXIDE; PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE; SODIUM DERIVATIVE;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; GRIGNARD REACTION; HYDROBORATION; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; SUZUKI REACTION; SWERN OXIDATION; SYNTHESIS;

EID: 33847301875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.044     Document Type: Article

References (53)

1. For several examples, see:
2. For Ciprofloxacin, see:. Grohe K., and Heitzer H. Liebigs Ann. Chem. (1987) 29
3. For Indinavir, see:. Dorsey B.D., Levin R.B., McDaniel S.L., Vacca J.P., Guare J.P., Darke P.L., Zugay J.A., Emini E.A., Schleif W.A., Quintero J.C., Lin J.H., Chen I.-W., Holloway M.K., Fitzgerald P.M.D., Axel M.G., Ostovic D., Anderson P.S., and Huff J.R. J. Med. Chem. 37 (1994) 3443
4. For Glivec, see:. Capdeville R., Buchdunger E., Zimmermann J., and Matter A. Nat. Rev. 1 (2002) 493
5. For a recent review, see:. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893
6. For a review, see:
7. Dinsmore C.J., and Beshore D.C. Tetrahedron 58 (2002) 3297 For leading references, see:
8. Kopple K., and Ghazarian H.J. J. Org. Chem. 33 (1968) 862
9. Nitecki D.E., Halpern B., and Westley J.W. J. Org. Chem. 33 (1968) 864
10. Grahl-Nielsen O. Tetrahedron Lett. (1969) 2827
11. Suzuki K., Sasaki Y., Endo N., and Mihara Y. Chem. Pharm. Bull. 29 (1981) 233
12. Ueda T., Saito M., Kato T., and Izumiya N. Bull. Chem. Soc. Jpn. 56 (1983) 568
13. Greenstein J.P., and Winitz M. Chemistry of the Amino Acids Vol. 2 (1961), Wiley, New York, NY p 793
14. For a review, see:. Dinsmore C.J., and Beshore D.C. Org. Prep. Proced. Int. 34 (2002) 367
15. For recent examples, see:
16. Binisti C., Assogba L., Touboul E., Mounier C., Huet J., Ombetta J.-E., Dong C.Z., Redeuilh C., Heymans F., and Godfroid J.-J. Eur. J. Med. Chem. 36 (2001) 809
17. Scapecchi S., Martini E., Manetti D., Ghelardini C., Martelli C., Dei S., Galeotti N., Guandalini L., Novella R.M., and Teodori E. Bioorg. Med. Chem. 12 (2004) 71
18. Berkheij M., van der Sluis L., Sewing C., den Boer D.J., Terpstra J.W., Hiemstra H., Iwema Bakker W.I., van den Hoogenband A., and van Maarseveen J.H. Tetrahedron Lett. 46 (2005) 2369
19. For several examples, see:
20. Mueller W., and Stauss U. Helv. Chim. Acta 65 (1982) 2118
21. Phillips G.B., Morgan Jr. T.K., Lumma Jr. W.C., Gomez R.P., Lind J.M., Lis R., Argentieri T., and Sullivan M.E. J. Med. Chem. 35 (1992) 743
22. Bigge C.F., Hays S.J., Novak P.M., Drummond J.T., Johnson G., and Bobovski T.P. Tetrahedron Lett. 30 (1989) 5193
23. Kempf, D. J.; Norbeck, D. W.; Sham, H. L. U.S. Patent 5,455,351, 1995.
24. For an asymmetric synthesis, see:. Warshawsky A.M., Patel M.V., and Chen T.-M. J. Org. Chem. 62 (1997) 6439
25. Brieden, W.; Roduit, J.-P. U.S. Patent 5,856,485, 1999;
26. Watkins W.J., Landaverry Y., Leger R., Litman R., Renau T.E., Williams N., Yen R., Zhang J.Z., Chamberland S., Madsen D., Griffith D., Tembe V., Huie K., and Dudley M.N. Bioorg. Med. Chem. Lett. 13 (2003) 4241
27. Orme, M. W.; Sawyer, J. S. U.S. Patent 6,825,197, 2004;
28. Balan, C.; Bo, Y.; Dominguez, C.; Fotsch, C. H.; Gore, V. K.; Ma, V. V.; Norman, M. H.; Ognyanov, V. I.; Qian, Y.-X.; Wang, X.; Xi, N.; Xu, S. PCT Int. Appl. WO 04035549, 2004.
29. The methyl ester of compound 7 will cyclize spontaneously at rt upon reduction with lithium borohydride. See: Ref. 16b.
30. For selected examples, see:
31. Hirai Y., Chintani M., Yamazaki T., and Momose T. Chem. Lett. (1989) 1449
32. Haddad M., Imogai H., and Larcheveque M. J. Org. Chem. 63 (1998) 5680
33. Chevliakov M.V., and Montgomery J. J. Am. Chem. Soc. 121 (1999) 11139
34. For closely related examples, see:
35. Kano S., Yokomatsu T., Yuasa Y., and Shibuya S. Heterocycles 24 (1986) 621
36. Thomas, R. C.; Cleek, G. J.; Hutchinson, D. K.; Yamada, H. U.S. Patent 5,922,707, 1999.
37. For N-alkyloxazolidinones, see:
38. Tamura, Y.; Kato, T. Japanese Patent 030049, 2002; For N-phenyloxazolidinones, see:
39. Fancher L.W., Gless Jr. R.D., and Wong R.Y. Tetrahedron Lett. 29 (1988) 5095
40. For reactions with thiols, see:
41. Kunde, K.; Herd, K.-J. U.S. Patent 5,410,081, 1995;
42. Ishibashi H., Uegaki M., and Sakai M. Synlett (1997) 915
43. Ishibashi H., Uegaki M., Sakai M., and Takeda Y. Tetrahedron 57 (2001) 2115
44. For amines, see:
45. Rooney, P. C.; Nutt, M. O. U.S. Patent 5,491,263, 1996; For an intramolecular example with anilines, see:
46. Poindexter G.S., Bruce M.A., LeBoulluec K.L., and Monkovic I. Tetrahedron Lett. 35 (1994) 7331
47. Aicher, T. D. l; Chen, Z.; Chen, Y.; Faul, M. M.; Krushinski, J. H., Jr.; Le H. Y.; Pineiro-Nunez, M. M.; Rocco, V. P.; Ruley, K. M.; Schaus, J. M.; Thompson, D. C.; Tupper, D. E. PCT Int. Appl. WO 03082877, 2003.
48. For synthesis of orthogonally protected 2-styrylpiperazines using Witting reactions with benzyltriphenylphosphonium halides, see: Hauske, J. R.; Aquila, B. M. PCT Int. Appl. WO 03016274, 2003.
49. For comparison to published data, see: Yoshikawa, S.; Emori, E.; Matsuura, F.; Clark, R.; Ikuta, H.; Yasuda, N.; Nagakura, T.; Yamazaki, K.; Aoki, M. European Patent Application 1338595, 2003.
50. For comparison to published data, see: Kobayashi, S.; Komoriya, S.; Haginoya, N.; Suzuki, M.; Yoshino, T.; Nagahara, T.; Nagata, T.; Horino, H.; Ito, M.; Mochizuki, A. U.S. Patent 6,747,023, 2004.
51. For comparison to published data, see: Fukatsu, K.; Nakayama, Y.; Tarui, N.; Mori, M.; Matsumoto, H.; Kurasawa, O.; Banno, H. European Patent 1661898, 2006.
52. For comparison to published data, see: Hamilton, A. D.; Ernst, J.; Orner, B. U.S. Patent 6,858,600, 2005.
53. For comparison to published data, see: Arkin, M. R.; McDowell, R. S.; Oslob, J. D.; Raimundo, B. C.; Waal, N. D.; Yu, C. H. U.S. Patent 6,806,279, 2004.