Advertisement

Chemistry of Natural Compounds

, Volume 49, Issue 4, pp 783–784 | Cite as

Reaction of d-Pseudoephedrine and 4-Morpholinylbenzaldehyde

  • S. D. Fazylov
  • A. E. Arinova
  • O. A. Nurkenov
  • I. V. Kulakov
Article

1,3-Oxazolidines are highly interesting because of their unique properties that allow them to be used in medicine and industry. They are also scientifically interesting as products of enantioselective synthesis of planar-chiral compounds [1, 2, 3]. We established previously the absolute configurations of the chiral centers of several 1,3-oxazolidines prepared from d- and l-ephedrines [4]. The various configurations of the chiral center in d- and l-ephedrines should produce various conformations of the oxazolidine ring of 2. According to several researchers [5, 6, 7, 8], the reaction of β-aminoalcohols with various aldehydes occurs usually stereoselectively or with formation of the S-stereoisomer or the R-epimer. The stereoselectivity depends usually on the nature of the reactants and solvents.

Herein we present results from a study of the reaction of d-threo-2-methylamino-1-phenyl-1-propanol (the alkaloid d-pseudoephedrine) ( 1) with previously unstudied 4-morpholinylbenzaldehyde,...

Keywords

Morpholine Chiral Center Pseudoephedrine Methine Proton Anhydrous Toluene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    A. H. Beckett and G. R. Jones, Tetrahedron, 33, 3313 (1977).CrossRefGoogle Scholar
  2. 2.
    S. A. Bourne, L. D. Fitz, R. P. Kashyap, M. Krawiec, R. B. Walker, W. H. Watson, and L. M. Williams, J. Chem. Crystallogr., 27, No. 1, 35–44 (1997).Google Scholar
  3. 3.
    N. S. Khruscheva, N. M. Loire, V. I. Sokolov, and V. D. Makhaev, J. Chem. Soc. Perkin Trans. 1, 2425 (1997).Google Scholar
  4. 4.
    S. D. Fazylov, A. M. Gazaliev, and O. A. Nurkenov, in: Selected Methods for Synthesis and Modification of Heterocycles [in Russian], V. G. Kartsev (ed.), IBS Press, Moscow, 2004, 2493 pp.Google Scholar
  5. 5.
    L. Neelakantan, J. Org. Chem., 16, 2256 (1971).CrossRefGoogle Scholar
  6. 6.
    S. M. Davtyan, G. L. Papayan, and M. A. Oganyan, Arm. Khim. Zh., 34, 242 (1984).Google Scholar
  7. 7.
    C. Agami and T. Rizk, J. Chem. Soc. Chem. Commun., 1485 (1983).Google Scholar
  8. 8.
    F. Santiesteban, C. Grimaldo, R. Conteras, and B. W. Meyer, J. Org. Chem., 16, 2252 (1971).Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • S. D. Fazylov
    • 1
  • A. E. Arinova
    • 1
  • O. A. Nurkenov
    • 1
  • I. V. Kulakov
    • 2
  1. 1.Institute of Organic Synthesis and Coal Chemistry of the Republic of KazakhstanKaragandaKazakhstan
  2. 2.F. M. Dostoevskii Omsk State UniversityOmskRussia

Personalised recommendations