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Synthesis 1987; 1987(5): 452-455
DOI: 10.1055/s-1987-33430
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Spiro Derivatives of Tetrahydrothiophene. Synthesis of the Quinolizidine <3-spiro-2′> tetrahydrothiophene System Using Solid/Liquid or Liquid/Liquid Phase-Transfer Catalysis

Jerzy T. Wróbel* , Elżbieta Hejchman
  • *Department of Chemistry, University of Warsaw, 1 Pasteur St., PL-02-093 Warsaw, Poland
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Publication Date:
18 September 2002 (online)

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4-Oxooctahydroquinolizine<3-spiro-2′>tetrahydrothiophene 1′,1′-dioxide can be synthetized from 2-cyanotetrahydrothiophene by two independent routes, both of them using phase-transfer catalysis: the first one involves alkylation of 2-cyanotetrahydrothiophene under PTC conditions, the second one N-acylation of 2-(2-chloroethyl)piperidine with 2-chlorocarbonyltetrahydrothiophene with the final cycloalkylation being performed under PTC conditions. Two stereoisomers of the spiro compound are obtained.