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Synthesis of 3-Vinylphenyl Ethyl(methyl)carbamate: A Potential Human Metabolite of Rivastigmine
Corresponding Author(s) : Fei Li
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Convenient and efficient syntheses of 3-vinylphenyl ethyl (methyl) carbamate, one of potential metabolites from rivastigmine, has been developed. The overall yield is higher than 30 % and represents the first direct synthesis of this metabolite from rivastigmine.
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References
J.L. Cummings and G. Cole, J. Am. Med. Assoc., 287, 2335 (2002).
P.T. Francis, A.M. Palmer, M. Snape and G.K. Wilcock, J. Neurol. Neurosur. Psychiatry, 66, 137 (1999).
G. Lefèvre, M. Büche, G. Sedek, S. Maton, A. Enz, U. Lorch, C. Sagan and S. Appel-Dingemanse, J. Clin. Pharmacol., 49, 430 (2009).
B.R. Williams,A. Nazarians and M.A. Gill, Clin. Ther., 25, 1634 (2003).
J. Bhatt, G. Subbaiah and S. Kambli, J. Chromatogr. B, 852, 115 (2007).
F. Pommier and R. Frigola, J. Chromatogr. B, 784, 301 (2003).
F. Zhang, M. Hu, M. Xie, A. Lai, R. Sun, D. Chen, R. Bao and H. Bai, Prepatation Method of Rivastigmine, Its Intermediates and Preparation Method of the Intermediates, US Patent 0286437 A1 (2010).
A. Gaitonde and M. Mangle, GB Patent 2409453A.
F. Deng, J.J. Lu, H.Y. Liu, L.P. Lin, J. Ding and J.S. Zhang, Chin. Chem. Lett., 22, 28 (2011).
Y. Hayashi, S. Orikasa, K. Tanaka, K. Kanoh and Y. Kiso, J. Org. Chem., 65, 8402 (2000).