Optical resolution and enantiomeric purity determination of the analgesic cizolirtine

✍ Scribed by Antoni Torrens; José A. Castrillo; Jordi Frigola; Leonardo Salgado; Jordi Redondo

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 158 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:1<63::aid-chir11>3.0.co;2-k

✦ Synopsis

The optical resolution of (±)-cizolirtine was accomplished with excellent results (>99% ee) by means of crystallization with (+)-or (-)-di-p-toluoyltartaric acid. The optical purity of the samples was controlled by three independent methods: 1 H NMR, capillary electrophoresis (CE) (using ␤-cyclodextrins as chiral resolving agents), and HPLC (using a glycoproteic column). The use of a rapid analytical technique like 1 H NMR for estimating the relative amounts of each enantiomer, together with the high sensitivity of CE, afforded a convenient strategy for monitoring the entire process leading to enantiopure compounds.