Skip to main content
SpringerLink
Log in

Synthesis of acetals containing a primary amino group

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Amino acetals of the general formula MeCH(OR)(OXNH2) (R = Et, Bu, X = CH2CH2, CH2CH2CH2, CH2CMe2) were synthesized in 53–91% yield by acid-catalyzed reaction of N-(2-hydroxyethyl)-, N-(3-hydroxypropyl)-, and N-(2-hydroxy-1,1-dimethylethyl)-2,2,2-trifluoroacetamides with vinyl ethers, followed by removal of the trifluoroacetyl protection by alkaline hydrolysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Yanovskaya, L.A., Yufit, S.S., and Kucherov, V.F., Khimiya atsetalei (The Chemistry of Acetals), Moscow: Nauka, 1975, p. 275; Mőhrle, H. and Kamper, Ch., Pharmazie, 1983, vol. 38, p. 512; Yamanoi, K., Ohfune, Y., Watanabe, K., Li, P.N., and Takeuchi, H., Tetrahedron Lett., 1988, vol. 29, p. 1181.

    Google Scholar 

  2. Povarov, L.S., Usp. Khim., 1965, vol. 34, p. 1489.

    Article  CAS  Google Scholar 

  3. Mikhant’ev, B.I., Mikhant’ev, V.B., Lapenko, V.L., and Voinova, V.K., Nekotorye vinil’nye monomery (Some Vinyl Monomers), Voronezh: Voronezh. Gos. Univ., 1970, p. 260.

    Google Scholar 

  4. Charya, S.B., Dutta, S., and Sanyal, U., J. Indian Chem. Soc., 1998, vol. 75, p. 46; Ottow, E., Huth, A., Neuhans, R., Schneider, H., Turski, L., and Dyrks, T., FRG Patent no. 19 617 862, 1997; Ref. Zh., Khim., 1999, no. 1 O 105 P; Burilov, A.R., Vagapova, L.I., Pudovik, M.A., and Konovalov, A.I., Russ. J. Gen. Chem., 2007, vol. 77, p. 649; Kasymova, E.M., Chugunova, E.A., Burilov, A.R., Yusupova, L.M., and Pudovik, M.A., Russ. J. Gen. Chem., 2007, vol. 77, p. 1312; Granik, V.G., Preparativnaya khimiya atsetalei amidov i laktamov (Preparative Chemistry of Amide and Lactam Acetals), Moscow: Vuzovskaya Kniga, 2011, p. 280.

    CAS  Google Scholar 

  5. Shostakovskii, M.F., Chekulaeva, I.A., and Gershtein, N.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1952, p.172.

  6. Shostakovskii, M.F. and Chekulaeva, I.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1953, p. 368.

  7. Shostakovskii, M.F. and Chekulaeva, I.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1955, p. 913.

  8. Minbaev, B.U., Aimakov, O.A., and Kabdulova, U.B., Zh. Obshch. Khim., 1976, vol. 46, p. 2389.

    CAS  Google Scholar 

  9. Shostakovskii, M.F. and Chekulaeva, I.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1955, p. 146; Shostakovskii, M.F. and Chekulaeva, I.A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1957, p. 75.

  10. Nedolya, N.A., Dymchenko, V.I., and Afonin, A.V., Zh. Org. Khim., 1994, vol. 30, p. 507; Nedolya, N.A., Zinov’eva, V.P., Komel’kova, V.I., and Trofimov, B.A., Zh. Org. Khim., 1994, vol. 30, p. 1173; Kukharev, B.F., Stankevich, V.K., and Klimenko, G.R., Usp. Khim., 1995, vol. 64, p. 56.

    CAS  Google Scholar 

  11. Mamedov, Sh., Shamilov, Kh.Kh., and Khydyrov, D.N., Biologicheski aktivnye soedineniya (Biologocally Active Compounds), Danilov, S.N., Ed., Moscow: Nauka, 1965, pp. 288, 294.

    Google Scholar 

  12. Trofimov, B.A., Geteroatomnye proizvodnye atsetilena (Heteroatom Acetylene Derivatives), Moscow: Nauka, 1981, p. 53.

    Google Scholar 

  13. Kukharev, B.F., Stankevich, V.K., and Kukhareva, V.A., Russ. J. Org. Chem., 2003, vol. 39, p. 622.

    Article  CAS  Google Scholar 

  14. Sintezy organicheskikh soedinenii (Syntheses of Organic Compounds), Nesmeyanov, A.N. and Bobrov, P.A., Eds., Moscow: Akad. Nauk SSSR, 1952, vol. 2, p. 15.

    Google Scholar 

  15. Barton, J.W., Protective Groups in Organic Chemistry, McOmie, J.F.W., Ed., London: Plenum, 1973. Translated under the title Zashchitnye gruppy v organicheskoi khimii, Moscow: Mir, 1976, p. 51.

    Google Scholar 

  16. Shim, M.S. and Kwon, Y.J., Biomacromolecules, 2008, vol. 9, p. 444.

    Article  CAS  Google Scholar 

  17. Kitayama, K., Iwasaki, H., Yoneda, K., and Oonishi, T., JPN Patent Appl. no. 82–77 234, 1996; Ref. Zh., Khim., 1998, no. 23 N 32 P.

  18. Lazarus, R.A. and Benkovic, S.J., J. Am. Chem. Soc., 1979, vol. 101, p. 4300.

    Article  CAS  Google Scholar 

  19. Svirskaya, P.I. and Leznoff, C.C., J. Org. Chem., 1987, vol. 52, p. 1362.

    Article  CAS  Google Scholar 

  20. Kostyanovsky, R.G., Lenev, D.A., Krutius, O.N., and Stankevich, A.A., Mendeleev Commun., 2005, no. 4, p. 140.

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. A. Lobanova, V. K. Stankevich & B. F. Kukharev

Authors
  1. N. A. Lobanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. K. Stankevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. F. Kukharev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. F. Kukharev.

Additional information

Original Russian Text © N.A. Lobanova, V.K. Stankevich, B.F. Kukharev, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1295–1301.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lobanova, N.A., Stankevich, V.K. & Kukharev, B.F. Synthesis of acetals containing a primary amino group. Russ J Org Chem 48, 1289–1296 (2012). https://doi.org/10.1134/S1070428012100053

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428012100053

Keywords

Search

Navigation