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Pure Appl. Chem., 2002, Vol. 74, No. 8, pp. 1359-1368

http://dx.doi.org/10.1351/pac200274081359

Development of a practical synthesis of sumanirole

Peter G. M. Wuts1*, Rui Lin Gu1, Jill M. Northuis1, Tricia A. Kwan1, Doris M. Beck2 and Michael J. White2

1 Chemical Process Research and Development, Pharmacia, Kalamazoo, MI 49001, USA
2 Bioprocess and Formulation Technology, Pharmacia, Kalamazoo, MI 49001, USA

Abstract: A new synthesis of sumanirole that is being developed to treat Parkinson's disease is described. The basic skeleton is constructed from 8-hydroxyquinoline and elaborated to the key tricylic intermediate 14. Further elaboration affords a 1,2-amino alcohol, which is converted to an aziridine by a new process. Finally, dissolving metal reduction to open the aziridine and protecting group removal affords sumanirole.