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An Efficient Synthesis of Racemic Tolterodine
Corresponding Author(s) : P. Muralikrishna
Asian Journal of Chemistry,
Vol. 26 No. 9 (2014): Vol 26 Issue 9
Abstract
The efficient and cost effective of the synthesis of (±)-tolterodine (1), a precursor of (+)-(R)-tolterodine was efficiently performed from 6-methyl-4-chroman-2-one (2) via 4 steps in high yield. This process is suitable for large-scale commercial production by avoiding hazardous reagents and high pressure of hydrogen gas.
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- U. Jonas, K. Höfner, H. Madersbacher and T.H. Holmdahl, World J. Urol., 15, 144 (1997); doi:10.1007/BF02201987.
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References
U. Jonas, K. Höfner, H. Madersbacher and T.H. Holmdahl, World J. Urol., 15, 144 (1997); doi:10.1007/BF02201987.
P.G. Gillberg, S. Sundquist and L. Nilvebrant, Eur. J. Pharmacol., 349, 285 (1998); doi:10.1016/S0014-2999(98)00214-3.
T. Yamanishi, C.R. Chapple and R. Chess-Williams, World J. Urol., 19, 299 (2001); doi:10.1007/s003450100226.
D.J. Sellers, T. Yamanishi, C.R. Chapple, C. Couldwell, K. Yasuda and R. Chess-Williams, J. Autonom. Pharmacol., 20, 171 (2000); doi:10.1046/j.1365-2680.2000.00181.x.
H. Hirose, I. Aoki, T. Kimura, T. Fujikawa, T. Numazawa, K. Sasaki, M. Nishikibe and K. Noguchi, Eur. J. Pharmacol., 452, 245 (2002); doi:10.1016/S0014-2999(02)02335-X.
L. Nilvebrant, K.E. Andersson, P.G. Gillberg, M. Stahl and B. Sparf, Eur. J. Pharmacol., 327, 195 (1997); doi:10.1016/S0014-2999(97)89661-6.
P.G. Andersson, H.E. Schink and K.J. Österlund, Org. Chem., 63, 8067 (1998); doi:10.1021/jo981259r.
J.E. Cabaj and J.R. Gage, Process to Prepare Tolterodine, US Patent 5,922,914 (1999).
C. Botteghi, T. Corrias, M. Marchetti, S. Paganelli and O. Piccolo, Org. Process Res. Dev., 6, 379 (2002); doi:10.1021/op020014k.
C. Selenski and T.R.R. Pettus, J. Org. Chem., 69, 9196 (2004); doi:10.1021/jo048703c.
L. Colombo, R. Rossi, G. Castaldi, P. Allegrini and S.P.A. Dipharma, Italian Patent MI2004A000616 (2004); Canadian Patent CA 2502640, (2005); European Patent EP1584621 (2005).
C. Hedberg and P.G. Andersson, Adv. Synth. Catal., 347, 662 (2005); doi:10.1002/adsc.200404234.
G. Chen, N. Tokunaga and T. Hayashi, Org. Lett., 7, 2285 (2005); doi:10.1021/ol0507367.
F. Ulgheri, M. Marchetti and O.J. Piccolo, Org. Chem., 72, 6056 (2007); doi:10.1021/jo0705667.