Abstract
Reaction of tert-butyl 4-oxopiperidine-1-carboxylate dimethylhydrazone with BuLi in the presence of N,N’-dimethylpropylene urea and subsequently with BrCH2CH=CRR’ (R=H, Me, Et; R’=CH2Ar) afforded in 50–80% yields the corresponding tert-butyl 3-alkenyl-4-oxopiperidine-1-carboxylates, promising synthons for preparation of diverse piperidine derivatives.
Similar content being viewed by others
References
Joule, J.A. and Mills, K., Heterocyclic Chemistry, Malden, MA: Blackwell Science, 2000.
The Art of Drug Synthesis, Johnson, D.S. and Li, J.J., Eds., Hoboken, NJ: Wiley, 2007.
Modern Drug Synthesis, Li, J.J. and Johnson, D.S., Eds., Hoboken, NJ: Wiley, 2010.
Yakhontov, L.N. and Glushkov, R.G., Sinteticheskie lekarstvennye sredstva (Synthetic Drugs), Moscow: Meditsina, 1983.
Hoover, D.J., Lefker, B.A., and Rosati, R.L., US Patent no. 5442044, 1995; EU Patent no. 438233, 1991.
Cordova, A. and Ibrahem, I., Angew. Chem. Int. Ed., 2006, vol. 45, p. 1952.
Corless, M., Maw, G.N., Planken, S., Platts, M.Y., Pryde, D.C., Sanderson, V., Stobie, A., Barber, Ch.G., Barker, L., Foster, L., Morren, D., Russell, R., Stacey, P., Van Der Graaf, P., Wayman, Ch., Beaumont, K., Coggon, S., Kohl, Ch., and Tute, M., J. Med. Chem., 2006, vol. 49, p. 4409.
Lymer, J., Portela-Cubillo, F., Scanlan, E.M., Walton, J.C., and Scott, J.S., Tetrahedron, 2008, vol. 64, p. 11908.
Adeel, M., Juma, B., Lander, P., Reinke, H., Villinger, A., Fisher, Ch., Langer, P., and Spannenberg, A., Adv. Synth. Catal., 2009, vol. 351, p. 1073.
Breit, B., Schmidt, S., and Usui, I., Org. Lett., 2009, vol. 11, p. 1453.
Burtoloso, A.C.B. and Carita, A., Tetrahedron Lett., 2010, vol. 51, p. 686.
Zhao, X., Liu, D., Guo, H., Liu, Y., and Zhang, W., J. Am. Chem. Soc., 2011, vol. 133, p. 19354.
Moskalenko, A.I. and Boev, V.I., Russ. J. Org. Chem., 2014, vol. 50, p. 1117.
Moskalenko, A.I. and Boev, V.I., Russ. J. Org. Chem., 2014, vol. 50, p. 953.
Zhao, L.M., Jin, H.S., Wan, L.J., and Zhang, L.M., J. Org. Chem., 2011, vol. 76, p. 1831.
Moskalenko, A.I. and Boev, V.I., Russ. J. Org. Chem., 2009, vol. 45, p. 895.
Miriyala, B., Bhattacharyya, S., and Williamson, J.S., Tetrahedron, 2004, vol. 60, p. 1463.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.I. Moskalenko, V.I. Boev, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 11, pp. 1599–1603.
Rights and permissions
About this article
Cite this article
Moskalenko, A.I., Boev, V.I. 3-allylation of tert-butyl 4-oxopiperidine-1-carboxylate. Russ J Org Chem 50, 1584–1589 (2014). https://doi.org/10.1134/S1070428014110086
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014110086