Practical synthesis of (S)-3-(p-nitrobenzyloxy-carbonylamino)pyrrolidine and its related compounds from L-aspartic acid

Heterocycles

Volumn 44, Issue 1, 1997, Pages 213-225

  Tomori, Hiroshi ^a   Shibutani, Kuniko ^b   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000362733     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-s10     Document Type: Article

References (31)

1. I. Kawamoto, R. Endo, M. Miyauchi, K. Ishikawa, K. Watanabe, H. Yasuda, S. Ohya, and Y. Utsui, Eur. Patent 1994, 560613 [Chem. Abstr., 1994, 120, 269926g].
2. (a) D. Bouzard, P. Di Cesare, M. Essiz, J. P. Jacquet, B. Ledoussal, P. Remuzon, R.E. Kassler, and J. Fung-Tomc, J. Med. Chem., 1992, 35, 518.
3. (b) S. L. Dax and C.-C. Wei, J. Org. Chem., 1992, 57, 744.
4. (c) B. Ledoussal, D. Bouzard, and E. Coroneos, J. Med. Chem., 1992, 35, 198.
5. (a) M. Iwata, T. Kimura, T. Inoue, Y. Fujihara, and T. Katsube, Eur. Patent 1990, 352123 [Chem. Abstr., 1990, 113, 78178k].
6. (b) U. Petersen, T. Schenke, M. Schriewer, A. Krebs, K. Grobe, I. Haller, K. G. Metzger, R. Endermann, and J. Hans, Eur. Patent 1990, 391169 [Chem. Abstr., 1991, 114, 185466v].
7. (c) P. Di Cesare, J. P. Jacquet, M. Essiz, P. Remuzon, D. Bouzard, and A. Weber, Eur. Patent 1988, 266576 [Chem. Abstr., 1990, 112, 118793v].
8. (d) J. P. Sanchez, J. M. Domagala, C. L. Heifetz, S. R. Priebe, J. A. Sesnie, and A. K. Trehan, J. Med. Chem., 1992, 35, 1764.
9. (e) T. Rosen, D. T. W. Chu, I. M. Lico, P. B. Fernandes, L. Shen, S. Borodkin, and A. G. Pernet, J. Med. Chem., 1988, 31, 1586.
10. (a) Y. Ito, H. Kato, and T. Sasaki, Jpn. Patent 1992, 178326 [Chem. Abstr., 1992, 117, 226309d].
11. (b) M. Takamatsu, M. Matsui, and Y. Ikeda, Eur. Patent 1989, 327709 [Chem. Abstr., 1990, 113, 71314t].
12. (c) D. T. Chu, J. J. Plattner, and R. Hallas, World Intellectual Patent 1992, 9203136 [Chem. Abstr., 1992, 117, 111620f].
13. (a) T. Hojo, T. Yokoyama, K. Nakazono, and M. Okada, Jpn. Patent 1990, 218664 [Chem. Abstr., 1991, 114, 81579t].
14. (b) J. Maddaluno, A. Corruble, V. Leroux, G. Pié, and P. Duhamel, Tetrahedron: Asymmetry, 1992, 3, 10.
15. (a) D. T. Witiak, Z. Muhi-Eldeen, N. Mahishi, O. P. Sethi, and C. Gerald, J. Med. Chem., 1971, 14, 24.
16. (b) T. Van Le, F. G. Spencer, and J. N. Wemple, US Patent 1993, 5177217 [Chem. Abstr., 1993, 118, 19154q].
17. C. T. C. Chen, K. M. Wan, and M. S. C. Chen, Ger. Patent 1985, 3431249 [Chem. Abstr., 1985, 103, 196416c].
18. K. Soai and H. Oyamada, Synthesis, 1984, 605.
19. 4OH (15 ml) in dioxane at 50 °C for 3 h gave 1b in a poor yield of 15%. Monitoring of this reaction by hplc showed that a considerable amount of benzyl alcohol was formed under these conditions.
20. P. Gmeiner, F. Orecher, C. Thomas, and K. Weber, Tetrahedron Lett., 1995, 36, 381.
21. B. Moreau, S. Lavielle, and A. Marquet, Tetrahedron Lett., 1977, 2591.
22. R. J. Sundberg, G. S. Hamilton, and J. P. Laurino, J. Org. Chem., 1988, 53, 976.
23. H. Ito, T. Taguchi, and Y. Hanzawa, J. Org. Chem., 1993, 58, 774.
24. (a) F. Garro-Helion, A. Merzouk, and F. Guibé, J. Org. Chem., 1993, 58, 6109.
25. (b) S. Lemaire-Audoire, M. Savignac, and J. P. Genêt, Tetrahedron Lett., 1995, 36, 1267.
26. Ru complexes has been reported to promote isomerization of N-allylamines to the corresponding N-enamines: T. Mitsudo, S.-W. Zhang, and N. Satake, Tetrahedron Lett., 1992, 33, 5533.
27. 4 resulted in the recovery of the starting material.
28. W. Grassmann, and E. Wünsch, Chem. Ber., 1958, 91, 449.
29. These reaction conditions were not optimized.
30. D. Keglevic, A. Kornhauser, and S. Valentekovic, Carbohyd. Res., 1972, 22, 245
31. N, Yasuda, T. Yamashita, and Y. Ariyoshi, Jpn. Patent 1974, 133301 [Chem. Abstr., 1975, 82, 171443u].