Synthesis 2024; 56(14): 2234-2238
DOI: 10.1055/a-2235-5080
paper

Short Synthesis of Dopamine Agonist Rotigotine

Chandra Shekhar
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
Santanu Karmakar
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
Prathama S. Mainkar
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
,
a   Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
› Author Affiliations
The authors thank the Council of Scientific and Industrial Research (CSIR), C.S. thanks the University Grants Commission (UGC), and SK thanks CSIR for a research fellowship. S. C. thanks the Science and Engineering Research Board (SERB), Government of India for J C Bose fellowship (SB/S2/JCB-002/2015).


Abstract

A practical and short synthesis of FDA approved drug, Rotigotine, is achieved in two steps from 5-methoxy-2-tetralone, which in turn was synthesised by [4+2] cycloaddition of the in situ generated methoxyaryne from its precursor aryl triflate with benzyloxybutadiene or from 4-methoxyindanone via ring expansion using trimethylsilyldiazomethane.

Supporting Information



Publication History

Received: 10 November 2023

Accepted after revision: 27 December 2023

Accepted Manuscript online:
27 December 2023

Article published online:
29 January 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Kolster KS, Kohnen R, Schollmayer E, Moller JC, Oertel WH. Mov. Disord. 2004; 19: 1432
    • 1b Gorgoraptis N, Mah YH, Machner B, Curry VS, Malhotra P, Michael MH, Cohen D, Simister R, Nair A, Kulinskaya E, Ward N, Greenwood R, Husain M. Brain 2012; 135: 2478
  • 2 Wilson SM, Wurst MG, Whatley MF, Daniels RN. ACS Chem. Neurosci. 2020; 11: 2506
  • 3 Trenkwalder C, Borreguero DG, Montagna P, Lainey E, de Weerd AW, Tidswell P, Zyhlarz GS, Telstad W, Strambi LF. J. Neurol. Neurosurg. Psychiatry 2004; 75: 92
    • 4a Park DY, Kim KH, Cheon CH. Adv. Synth. Catal. 2018; 360: 462
    • 4b Webster R, Boyer A, Fleming MJ, Lautens M. Org. Lett. 2010; 12: 5148
    • 4c Citoler J, Harawa V, Marshall JR, Bevinakatti H, Finnigan JD, Charnock SJ, Turner NJ. Angew. Chem. Int. Ed. 2021; 60: 24456
  • 5 Zhou CQ, Li SS, Chen ZM, Li FQ, Lei P, Peng GG. PLoS One 2013; 8: e69738
    • 6a Venkatesh T, Mainkar PS, Chandrasekhar S. Org. Biomol. Chem. 2019; 17: 2192
    • 6b Chandrasekhar S, Reddy MV. Tetrahedron 2000; 56: 1111
    • 6c Anugu RR, Mainkar PS, Sridhar B, Chandrasekhar S. Org. Biomol. Chem. 2016; 14: 1332
    • 7a Krel M, Lallemand JY, Guillou C. Synlett 2005; 2043
    • 7b Cobley CJ, Evans G, Fanjul T, Simmonds S, Woods A. Tetrahedron Lett. 2016; 57: 986
    • 8a He X, Guo J, Wang Y, Tang W, Zhang X, Wang X, Wang Y. Patent WO2011/026318, 2011
    • 8b Olondriz FM, Marco MP. Patent US 2011/0152543 A1, 2011
    • 9a Chen T, Zou Y, Hu Y, Zhang Z, Wei H, Wei L, Zhang W. Angew. Chem. Int. Ed. 2023; 62: e202303488
    • 9b Salomy E, Orgue S, Riera A, Verdaguer X. Angew. Chem. Int. Ed. 2016; 55: 798
    • 11a Wu C, Fang Y, Larock RC, Shi F. Org. Lett. 2010; 12: 2234
    • 11b Li X, Sun Y, Huang X, Zhang L, Kong L, Peng B. Org. Lett. 2017; 19: 838
    • 11c Roy T, Biju AT. Chem. Commun. 2018; 54: 2580
  • 12 Liu C, Deng G, Li X, Xu Y, Yu K, Chen W, Zhang H, Yang X. Eur. J. Org. Chem. 2020; 20: 483
  • 13 Liu W, Buck M, Chen N, Shang M, Taylor NJ, Asoud J, Wu X, Hasinoff BB, Dmitrienko GI. Org. Lett. 2007; 9: 2915
    • 14a Liu H, Sun C, Lee NK, Henry RF, Lee D. Chem. Eur. J. 2012; 18: 11889
    • 14b Donthamsetti PC, Winter N, Schönberger M, Levitz J, Stanley C, Javitch JA, Isacoff EY, Trauner D. J. Am. Chem. Soc. 2017; 139: 18522