Advertisement

Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1795–1807 | Cite as

N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines

  • D. A. GruzdevEmail author
  • S. A. Vakarov
  • G. L. Levit
  • V. P. Krasnov
Article

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.

Keywords

amines (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine N-tosyl-(S)-proline acylation diastereoisomers kinetic resolution stereoselectivity 

Notes

The work was performed with financial support from the Russian Foundation for Basic Research (grants 12-03-31615, 12-03-33029, 13-03-00674), the Ural Branch of the Russian Academy of Sciences (project 12-P-3-1030), and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).

The authors are grateful to L. Sh. Sadretdinova for performing the HPLC analyses, and to Cand. Chem. Sci. M. I. Kodess for the recording of NMR spectra.

References

  1. 1.
    A. R. Katritzky, S. Rachwal, and B. Rachwal, Tetrahedron, 52, 15031 (1996).CrossRefGoogle Scholar
  2. 2.
    J. Ilaš, P. Štefanič Anderluh, M. Sollner Dolenc, and D. Kikelj, Tetrahedron, 61, 7325 (2005).CrossRefGoogle Scholar
  3. 3.
    S. Anas and H. B. Kagan, Tetrahedron: Asymmetry, 20, 2193 (2009).CrossRefGoogle Scholar
  4. 4.
    H. B. Kagan and J. C. Fiaud, Top. Stereochem., 18, 249 (1988).Google Scholar
  5. 5.
    C. E. Müller and P. R. Schreiner, Angew. Chem., Int. Ed., 50, 6012 (2011).CrossRefGoogle Scholar
  6. 6.
    V. P. Krasnov, D. A. Gruzdev, and G. L. Levit, Eur. J. Org. Chem., 1471 (2012).Google Scholar
  7. 7.
    J. H. Lee, K. Han, M.-J. Kim, and J. Park, Eur. J. Org. Chem., 999 (2010).Google Scholar
  8. 8.
    E. Busto, V. Gotor-Fernández, and V. Gotor, Chem. Rev., 111, 3998 (2011).CrossRefGoogle Scholar
  9. 9.
    S. Arai, S. Bellemin-Lapponnaz, and G. Fu, Angew. Chem., Int. Ed., 40, 234 (2001).CrossRefGoogle Scholar
  10. 10.
    C. K. De, E. G. Klauber, and D. Seidel, J. Am. Chem. Soc., 131, 17060 (2009).CrossRefGoogle Scholar
  11. 11.
    M. Binanzer, S.-Y. Hsieh, and J. W. Bode, J. Am. Chem. Soc., 133, 19698 (2011).CrossRefGoogle Scholar
  12. 12.
    C. Sabot, P. V. Subhash, A. Valleix, S. Arseniyadis, and C. Mioskowski, Synlett, 268 (2008).Google Scholar
  13. 13.
    A. Karnik and S. Kamath, Tetrahedron: Asymmetry, 19, 45 (2008).CrossRefGoogle Scholar
  14. 14.
    V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Korolyova, M. I. Kodess, V. N. Charushin, and O. N. Chupakhin, Tetrahedron: Asymmetry, 14, 1985 (2003).CrossRefGoogle Scholar
  15. 15.
    D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, and V. N. Charushin, Tetrahedron: Asymmetry, 21, 936 (2010).CrossRefGoogle Scholar
  16. 16.
    D. A. Gruzdev, G. L. Levit, M. I. Kodess, and V. P. Krasnov, Khim. Geterotsikl. Soedin., 805 (2012). [Chem. Heterocycl. Compd., 48, 748 (2012).]Google Scholar
  17. 17.
    D. A. Gruzdev, G. L. Levit, and V. P. Krasnov, Tetrahedron: Asymmetry, 23, 1640 (2012).CrossRefGoogle Scholar
  18. 18.
    V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Korolyova, M. I. Kodess, O. N. Chupakhin, M. H. Kim, H. S. Lee, Y. J. Park, and K.-C. Kim, Tetrahedron: Asymmetry, 10, 2691 (1999).CrossRefGoogle Scholar
  19. 19.
    Е. N. Chulakov, G. L. Levit, A. A. Tumashov, L. Sh. Sadretdinova, and V. P. Krasnov, Khim. Geterotsikl. Soedin., 779 (2012). [Chem. Heterocycl. Compd., 48, 724 (2012).]Google Scholar
  20. 20.
    D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, and V. P. Krasnov, Tetrahedron: Asymmetry, 24, 1240 (2013).CrossRefGoogle Scholar
  21. 21.
    T. Kawabata, M. Nagato, K. Takasu, and T. Fuji, J. Am. Chem. Soc., 119, 3169 (1997).CrossRefGoogle Scholar
  22. 22.
    D. Terakado and T. Oriyama, Org. Synth., 83, 70 (2006).Google Scholar
  23. 23.
    G. Priem, B. Pelotier, S. J. F. Macdonald, M. S. Anson, and I. B. Campbell, J. Org. Chem., 68, 3844 (2003).CrossRefGoogle Scholar
  24. 24.
    C. Ó. Dálaigh, S. J. Hynes, J. A. O’Brien, T. McCabe, D. J. Maher, C. W. Watson, and S. J. Connon, Org. Biomol. Chem., 4, 2785 (2006).CrossRefGoogle Scholar
  25. 25.
    G. V. Shustov, S. N. Denisenko, M. A. Shohen, and R. G. Kostyanovsky, Izv. Akad. Nauk SSSR, Ser. Khim., 1862 (1988). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 37, 1665 (1988).]Google Scholar
  26. 26.
    Z.-X. Xu, C. Zhang, Y. Yang, C.-F. Chen, and Z.-T. Huang, Org. Lett., 10, 477 (2008).CrossRefGoogle Scholar
  27. 27.
    I. Shiina, K. Nakata, K. Ono, Y. S. Onda, and M. Itagaki, J. Am. Chem. Soc., 132, 11629 (2010).CrossRefGoogle Scholar
  28. 28.
    B. Hu, M. Meng, Z. Wang, W. Du, J. S. Fossey, X. Hu, and W.-P. Deng, J. Am. Chem. Soc., 132, 17041 (2010).CrossRefGoogle Scholar
  29. 29.
    D. Belmessieri, C. Joannesse, P. A. Woods, C. MacGregor, C. Jones, C. D. Campbell, C. P. Johnston, N. Duguet, C. Concellón, R. A. Bragg, and A. D. Smith, Org. Biomol. Chem., 9, 559 (2011).CrossRefGoogle Scholar
  30. 30.
    X. Yang, V. D. Bumbu, P. Liu, X. Li, H. Jiang, E. W. Uffman, L. Guo, W. Zhang, X. Jiang, K. N. Houk, and V. B. Birman, J. Am. Chem. Soc., 134, 17605 (2012).CrossRefGoogle Scholar
  31. 31.
    K. Sakano, S. Yokohama, I. Hayakawa, S. Atarashi, and S. Kadoya, Agric. Biol. Chem., 51, 1265 (1987).CrossRefGoogle Scholar
  32. 32.
    S. Atarashi, S. Yokohama, K. Yamazaki, K. Sakano, M. Imamura, and I. Hayakawa, Chem. Pharm. Bull., 35, 1896 (1987).CrossRefGoogle Scholar
  33. 33.
    J. F. Bower, P. Szeto, and T. Gallagher, Org. Lett., 9, 3283 (2007).CrossRefGoogle Scholar
  34. 34.
    M. K. Parai and G. Panda, Tetrahedron Lett., 50, 4703 (2009).CrossRefGoogle Scholar
  35. 35.
    P. A. Slepukhin, D. A. Gruzdev, Е. N. Chulakov, G. L. Levit, V. P. Krasnov, and V. N. Charushin, Izv. Akad. Nauk SSSR, Ser. Khim., 932 (2011). [Russ. Chem. Bull., 60, 955 (2011).]Google Scholar
  36. 36.
    L. J. Xie, Chin. Chem. Lett., 6, 857 (1995).Google Scholar
  37. 37.
    M. Rueping, M. Stoeckel, E. Sugiono, and T. Theissmann, Tetrahedron, 66, 6565 (2010).CrossRefGoogle Scholar
  38. 38.
    K. Tsuji and H. Ishikawa, Synth. Commun., 24, 2943 (1994).CrossRefGoogle Scholar
  39. 39.
    I. Hayakawa, T. Hiramitsu, and Y. Tanaka, EP Pat. Appl. 0047005.Google Scholar
  40. 40.
    W. Oldham and I. B. Johns, J. Am. Chem. Soc., 61, 3289 (1939).CrossRefGoogle Scholar
  41. 41.
    N. Izumiya, Bull. Chem. Soc. Jpn., 23, 53 (1953).CrossRefGoogle Scholar
  42. 42.
    D. Armenise, G. Trapani, F. Stasi, and F. Morlacchi, Arch. Pharm., 331, 54 (1998).CrossRefGoogle Scholar
  43. 43.
    R. A. Bunce, D. M. Herron, and L. Y. Hale, J. Heterocycl. Chem., 40, 1031 (2003).CrossRefGoogle Scholar
  44. 44.
    G. Barker, G. P. Ellis, and D. A. Wilson, J. Chem. Soc. C, 2079 (1971).Google Scholar
  45. 45.
    E. Bamberger and H. Sternitzki, Ber. Dtsch. Chem. Ges., 26, 1291 (1893).CrossRefGoogle Scholar
  46. 46.
    D. E. Ames, H. R. Ansari, A. D. G. France, A. C. Lovesey, B. Novitt, and R. Simpson, J. Chem. Soc. C, 3088 (1971).Google Scholar
  47. 47.
    H. Bunsel, Ber. Dtsch. Chem. Ges., 22, 1053 (1889).CrossRefGoogle Scholar
  48. 48.
    R. A. Johnson, J. Org. Chem., 33, 3627 (1968).CrossRefGoogle Scholar
  49. 49.
    A. Thurkauf, P. Hillery, A. E. Jacobson, and K. C. Rice, J. Org. Chem., 52, 5466 (1987).CrossRefGoogle Scholar
  50. 50.
    R. G. Kostyanovsky, A. E. Polyakov, G. V. Shustov, K. S. Zaharov, and V. I. Markov, Dokl. Akad. Nauk SSSR, 219, 873 (1974). [Dokl. Chem., 219, 873 (1974).]Google Scholar
  51. 51.
    F. Beecham, J. Am. Chem. Soc., 79, 3257 (1957).CrossRefGoogle Scholar
  52. 52.
    R. C. Clark and J. S. Reid, Acta Crystallogr., Sect. A: Found. Crystallogr., A51, 887 (1995).Google Scholar
  53. 53.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • D. A. Gruzdev
    • 1
    Email author
  • S. A. Vakarov
    • 1
  • G. L. Levit
    • 1
  • V. P. Krasnov
    • 1
  1. 1.I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations