Collect. Czech. Chem. Commun. 1998, 63, 803-812

Synthesis and Crystal Structure of Pergolide Sulfoxide

Jan Čejkaa, Zdeněk Horákb, Svetlana Pakhomovaa, Bohumil Kratochvíla, Petr Sedmerac, Vladimír Havlíčekc, Ladislav Cvakb and Alexandr Jegorovd

a Department of Solid State Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
b Galena Co., 747 70 Opava-Komárov, Czech Republic
c Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20 Prague 4, Czech Republic
d Galena Co., Research Unit, Branišovská 31, 370 05 České Budějovice, Czech Republic


Pergolide sulfoxide (1), a metabolite of pergolide (2), has been prepared by oxidation of 2 with hydrogen peroxide. Its structure was determined by X-ray diffraction and compared with the structures of related ergot alkaloids. Two molecules of pergolide (S)- and (R)-sulfoxide crystallize with one molecule of water in the orthorhombic space group P212121 with a = 12.216(3) Å, b = 13.733(2) Å, c = 22.186(6) Å, Z = 4, V = 3 722(2) Å3.

Keywords: Ergot alkaloids; Pergolide sulfoxide; X-Ray crystal structure; NMR spectroscopy.