DOI QR코드

DOI QR Code

A short Synthesis of Trimebutine, 2-Dimethylamino-2-phenylbutyl3,4,5-trimethylbenzoate

  • Kim, Jin-Yeon (Department of Chemistry, Seonam University) ;
  • An, Gwang-Il (Laboratory of Cyclotron Application, Korea Institute of Radiological & Medical Sciences) ;
  • Chun, Kwon-Soo (Laboratory of Cyclotron Application, Korea Institute of Radiological & Medical Sciences) ;
  • Rhee, Hak-June (Department of Chemistry, Hanyang University)
  • Published : 2005.02.20

Abstract

Keywords

References

  1. Abei, T.; Isogai, S.; Ohnuki, H.; Okada, T.; Osada, M.; Kawamura, K.; Kiryu, Y.; Koizumi, H.; Suzuki, K.; Takagi, S.; Takahashi, Y.; Tsuchiya, M.; Nakamura, K.; Nanbu, T.; Muramatsu, M.; Yokoi, Y.; Yokota, H. Clinical Evaluation 1977, 5, 189
  2. Miyoshi, A.; Fukumoto, S.; Kita, S.; Harada, H.; Kishi, S.; Yamamoto, T.; Kakajima, T.; Moriga, M.; Suyama, T.; Kakazawa, S.; Nazen, S.; Hori, R.; Kamisiro, A. Jpn. Arch. Internal. Med. 1980, 27, 169
  3. Mazzone, O.; Trovato, G. M.; Mandala, M. L.; Monello, S. Clin. Ter. 1980, 95, 629
  4. Takenaga, H.; Magaribuchi, T.; Tamaki, H. Jpn. J. Pharmacol. 1984, 34, 177 https://doi.org/10.1254/jjp.34.177
  5. Luttecke, K. J. Int. Med. Res. 1978, 6, 86 https://doi.org/10.1177/030006057800600202
  6. Moshal, M. G.; Herron, M. J. Int. Med. Res. 1979, 7, 231
  7. Luttecke, K. Curr. Med. Res. Opin. 1980, 6, 437 https://doi.org/10.1185/03007998009109464
  8. Frexinos, J.; Fioramonti, J.; Bueno, L. Eur. J. Clin. Pharmacol. 1985, 28, 181 https://doi.org/10.1007/BF00609689
  9. Poitras, P.; Honde, C.; Havrankova, J.; Lahaie, R. G.; Trudel, L.; Goyer, R.; Junien, J. L.; Pascaud, X. Am. J. Physiol. 1986, 251, G349
  10. Boige, N.; Cargill, G.; Mashako, L.; Cezard, J. P.; Navarro, J. J. Ped. Gastroenterol. Nutr. 1987, 6, 548 https://doi.org/10.1097/00005176-198707000-00010
  11. Laboue, B.; Bulliard, M.; Frein, S.; Rouissiasse, S. WO Patent 0121601, 2001
  12. Martin, A.; Figadere, B.; Saivin, S.; Houin, G.; Chomard, J. M.; Cahiez, G. Arzneim. -Forsch. 2000, 50, 544
  13. Sai, H.; Ozaki, Y.; Hayashi, K.; Onoda, Y.; Yamada, K. Chem. Pharm. Bull. 1996, 44, 1168 https://doi.org/10.1248/cpb.44.1168
  14. Fukui, H.; Kobayashi, T.; Kaneda, O.; Ueda, M.; Yamato, E. JP Patent 58105946, 1983
  15. Spickett, R. G. W.; Vega Noverola, A.; Prieto Soto, J. GB Patent 1434826, 1976
  16. Torossian, D. R.; Aubard, G. G. DE Patent 2151716, 1972
  17. Torossian, D. R.; Aubard, G. G. DE Patent 2151718, 1972
  18. Yamazaki, S.; Yumoto, H. JP Patent 2001121165, 2001
  19. Toda, F. JP Patent 11080143, 1999
  20. Toda, F.; Kanemoto, K. Heterocycles 1997, 46, 185 https://doi.org/10.3987/COM-97-S69
  21. Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 2723 https://doi.org/10.1016/S0957-4166(97)00309-1
  22. Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 10, 999
  23. Borredon, E.; Clavellinas, F.; Delmas, M.; Gaset, A.; Sinisterra, J. V. J. Org. Chem. 1990, 55, 501 https://doi.org/10.1021/jo00289a022
  24. Shiryaev, A. K.; Moiseev, I. K. Zh. Obshch. Khim. 1988, 58, 1680
  25. Hiyama, T.; Mishima, T.; Sawada, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 1626 https://doi.org/10.1021/ja00839a086
  26. Merz, A.; Maerkl, G. Angew. Chem. 1973, 85, 867
  27. Baumgarten, H. E. Organic Syntheses; John Wiley: New York, 1973; Coll. Vol. 5, p 755
  28. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; John Wiley: New York, 1967; Vol. 1, p 314, and references therein
  29. Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970 https://doi.org/10.1021/jo9701445
  30. Adofsson, H.; Moberg, C. Tetrahedron: Asymmetry 1995, 6, 2023 https://doi.org/10.1016/0957-4166(95)00263-O
  31. Leung, W.-H.; Chow, E. K. F.; Wu, M.-C.; Kum, P. W. Y.; Yeung, L.-L. Tetrahedron Lett. 1995, 36, 107 https://doi.org/10.1016/0040-4039(94)02177-D
  32. Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem. 1991, 56, 5939 https://doi.org/10.1021/jo00020a042
  33. Chini, M.; Crotti, P.; Flippin, L. A.; Macchia, F. J. Org. Chem. 1991, 56, 7043 https://doi.org/10.1021/jo00025a018
  34. Blandy, C.; Choukroun, R.; Gervais, D. Tetrahedron Lett. 1983, 24, 4189 https://doi.org/10.1016/S0040-4039(00)88295-7
  35. Overman, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 22, 195 https://doi.org/10.1016/0040-4039(81)80053-6
  36. Ramachandran, P. V.; Krzeminski, M. P. Tetrahedron Lett. 1999, 40, 7879 https://doi.org/10.1016/S0040-4039(99)01642-1
  37. Ranu, B. C.; Jana, U. H. J. Org. Chem. 1998, 63, 8212 https://doi.org/10.1021/jo980793w
  38. Ooi, T.; Maruoka, K.; Yamamoto, H. Org. Synth. 1995, 72, 95 https://doi.org/10.15227/orgsyn.072.0095
  39. Maruoka, K.; Nagahara, S.; Ooi, T.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 5607 https://doi.org/10.1016/S0040-4039(01)93811-0
  40. Cecchi, P.; Pizzabiocca, A.; Renzi, G.; Chini, M.; Crotti, P.; Macchia, F.; Speranza, M. Tetrahedron 1989, 45, 4227 https://doi.org/10.1016/S0040-4020(01)81317-X
  41. Alvarez Ibarra, C.; Arias, S.; Fernandez, M. J.; Sinisterra, J. V. F. Q. J. Chem. Soc., Perkin Trans 2 1989, 503
  42. Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 6431 https://doi.org/10.1021/ja00198a070
  43. Naruse, Y.; Esaki, T.; Yamamoto, H. Tetrahedron 1988, 44, 4747 https://doi.org/10.1016/S0040-4020(01)86177-9
  44. Fields, T. L.; Lin, Y. I.; Warren, J. D.; Lang Jr., S. A. J. Heterocycl. Chem. 1988, 25, 1917 https://doi.org/10.1002/jhet.5570250656
  45. Harde, C.; Bohlmann, F. Tetrahedron 1988, 44, 81 https://doi.org/10.1016/S0040-4020(01)85095-X
  46. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923 https://doi.org/10.1021/jo00408a041
  47. Armarego, W. L. F.; Perin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: 1996

Cited by

  1. A Short Synthesis of Trimebutine, 2-Dimethylamino-2-phenylbutyl 3,4,5-Trimethylbenzoate. vol.36, pp.26, 2005, https://doi.org/10.1002/chin.200526051
  2. Crystal structure, Hirshfeld surface, spectroscopic analyses, electronic properties, NLO profile and thermochemical study of an antispasmodic agent trimebutine vol.1199, pp.None, 2005, https://doi.org/10.1016/j.molstruc.2019.127043