Share This Article:

A Simple and Highly Efficient Enantioselective Synthesis of (S)-Rivastigmine

Abstract Full-Text HTML Download Download as PDF (Size:197KB) PP. 26-32
DOI: 10.4236/ijoc.2011.12005    6,590 Downloads   14,321 Views   Citations

ABSTRACT

A highly efficient and convenient procedure for the enantioselective synthesis of (S)-Rivastigmine, a cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer’s type and dementia due to Parkinson’s disease, is accomplished by the treatment of versatile, readily accessible (S)-(-)-2-methyl-2-propanesulfinamide with 3-hydroxyacetophenone. This protocol provides high yield and excellent enantiomeric excess in short step synthesis.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

V. Arava, L. Gorentla and P. Dubey, "A Simple and Highly Efficient Enantioselective Synthesis of (S)-Rivastigmine," International Journal of Organic Chemistry, Vol. 1 No. 2, 2011, pp. 26-32. doi: 10.4236/ijoc.2011.12005.

References

[1] N. C. Berchtold, C. W. Cotman, “Evolution in the conceptualization of dementia and Alzheimer’s disease: Greco-Roman period to the 1960s,” Neurobiol. Aging. Vol. 19, No. 3, 1998, 173-189.
[2] J. Corey-Bloom, R. Anand, J. Veach, “A randomized trial evaluating the efficacy and safety of ENA 713 (rivastigmine tartarate), a new acetylcholinesterase inhibitor, in patients with mild to moderately severe Alzheimer’s disease,” Int. J. Geriatr. Psychopharmacol. Vol. 1, 1998, 55-65.
[3] M. Rosler, R. Anand, A. Cicin-Sain, S. Gauthier, Y. Agid, P. Dal-Bianco, H. B. St?helin, R. Hartman, M. Gharabawi, “Efficacy and safety of rivastigmine in patients with Alzheimer's disease: international randomized controlled trial,” Br. Med. J. Vol. 318, 1999, 633-640.
[4] S. I. Finkel, “Effects of rivastigmine on behavioral and psychological symptoms of dementia in Alzheimer’s disease,” Clin. Ther. Vol. 26, 2004, 980-990.
[5] M. Rosler, W. Retz, P. Retz-Junginger, H. J. Dennler, “Effects of two-year treatment with the cholinesterase inhibitor rivastigmine on behavioural symptoms in Alzheimer’s disease,” Behav. Neurol. Vol. 11, No. 4, 1998, 211-216.
[6] M. Emre, D. Aarsland, A. Albanese, “Rivastigmine for dementia associated with Parkinson’s disease,” N. Engl. J. Med. Vol. 315, 2004, 2509-2518.
[7] C. Gabelli, “Rivastigmine: an update on therapeutic efficacy in Alzheimer's disease and other conditions,” Curr. Med. Res. & Opin. Vol. 19, No. 2, 2003, 69-82.
[8] M. Wakayama, J. A. Ellman, “Recycling the tert-Butanesulfinyl Group in the Synthesis of Amines Using tert-Butanesulfinamide,” J. Org. Chem. Vol. 74, 2009, 2646-2650.
[9] M. T. Robak, M. A. Herbage, J. A. Ellman, “Synthesis and Applications of tert-Butanesulfinamide,” Chem. Rev. Vol. 110, No. 6, 2010, 3600-3740.
[10] A. V. Reddy, S. U. B. Rao, G. L. Narasimha, P. K. Dubey, “Improved process for the preparation of Tamsulosin Hydrochloride,” Synth. Commun. Vol. 39, 2009, 1451-1456.
[11] A. Gaitonde, M. Mangle, S. R. Pawar, “Novel process for the preparation of aminoalkyl phenyl carbamates,” PCT, WO 2005061446, 2005; Chem. Abstr. Vol. 143, 2005, 77963.
[12] H. Stepankova, J. Hajicek, S. Simek, “A method of production of (-)-(S)-3-[1-(dimethylamino) ethyl] phenyl-N-ethyl-N-methylcarbamate,” PCT, WO 2004037771, 2004; Chem. Abstr. Vol. 142, 2004, 6315.
[13] M. J. V. Garrido, A. M. Montserrat, M. J. Juarez, “Method of obtaining phenyl carbamates,” PCT, WO 2007014973, 2007; Chem. Abstr. Vol. 146, 2007, 206113.
[14] J. Feng, W-M. Chen, Sun, Ping-Hua, “Synthesis of S-(+)-rivastigmine hydrogen tartarate,” J. South. Med. Univ. Vol. 27, 2007, 177-180.
[15] A. A. Boezio, J. Pytkowicz, A. Cote, A. B. Charette, “Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine)monoxide chiral ligand,” J. Am. Chem. Soc. Vol. 125, 2003, 14260-14261.
[16] M. Hu, F. L. Zhang, M. H. Xie, “Novel Convenient Synthesis of Rivastigmine,” Synth. Commun. Vol. 39, 2009, 1527-1533.
[17] J. M. Sanchez, M. R. Mata, E. Busto, V. G. Fernandez, V. Gotor, “Chemoenzymatic Synthesis of Rivastigmine Based on Lipase-Catalyzed Processes,” J. Org. Chem. Vol. 74, 2009, 5304-5310.
[18] K. Han, C. Kim, J. Park, M-J. Feng, “Chemoenzymatic synthesis of rivastigmine via dynamic kinetic resolution as a key step,” J. Org. Chem. Vol. 75, 2010, 3105-3108.
[19] K. A. Kumar, M. A. Reddy, T. S. Kumar, B. V. Kumar, K. B. Chandrasekhar, P. R. Kumar, M. Pal, “Achiral bis-imine in combination with CoCl2: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol,” Beilstein. J. Org. Chem. Vol. 6, 2010, 1174 -1179.
[20] M. Fuchs, D. Koszelewski, K. Tauber, W. Kroutil, K. Faber, “Chemoenzymatic asymmetric total synthesis of (S)-Rivastigmine using ω-transaminases,” Chem. Commun. Vol. 46, 2010, 5500-5502.
[21] D. Guijarro, O. Pablo, M. Yus, “Asymmetric Synthesis of Chiral Primary Amines by Transfer Hydrogenation of N-(tert-Butanesulfinyl) ketimines,” J. Org. Chem. Vol.75, 2010, 5265-5270.
[22] A. V. Reddy, G. Laxminarasimhulu, P. K. Dubey, “Facile enantioselective synthesis of (S)-Rivastigmine & (+)-NPS-R-568 a calcimimetic agent,” Der Pharma Chemica. Vol. 3 (1), 2011, 426-433.
[23] A. V. Reddy, “Developing Chemical Processes for Active Pharmaceutical Ingredients (API’s)”, Third International conference and exhibition, Mumbai, India, January 10-11, 2011: Abstract No. 3.

  
comments powered by Disqus

Copyright © 2019 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.