Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate

✍ Scribed by László Ladányi; Ilona Sztruhár; Zoltán Budai; Gyula Lukács; Tibor Mezei; Gyula Argay; Alajos Kálmán; Gyula Simig

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 129 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:9<689::aid-chir4>3.0.co;2-x

✦ Synopsis

The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2, (-

), is described. The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X-ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 µm) and hexane-ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed.