Purification and Oxidation Reaction of Cinchona Alkalids

• Main Author: Siti Aisah, Iis
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/37846
• Institution: Institut Teknologi Bandung

The skeleton of 1-azabicyclo[2.2.2]oktana is an important moiety on some medicines having activities to cure headache, migrain, allergy, diarhoe, anti depression, etc. Cinchona alkaloids which are produced in large amount, especially in Indonesia, contains this bicyclo ring. In 1996, H.M.R. Hoffmann was succeed to degradate quinine and quinidin furnished quincorin and quincoridin using LiAlH4 as reagent. Quincorin and quincoridin could be come a precursor for the medicines having 1-azabisiklo[2.2.2]oktana moiety and as asymmetric catalyst. Unfortunately, the reaction using LiAlH4 is expensive and needs a certain condition. Therefore, the aim of this work is to find an alternative method for degradation of Cinchona alkaloids by using cheaper and milder condition. First step of this work was the oxidation of hydroxy group at C-9 on quinine and cinchonine in acetic acid which yielded quinotoxin and cinchonotoxin,respectively. Infrared spectrum showed peak at 1689,64 cm-1 and 1691,57 cm- 1 for carbonyl group of quinotoxin and cinchonotoxin, respectively. Furthermore, the optical rotation of the products are + 15o dan + 14o for quinotoxin and cinchonotoxin, respectively. This reaction is a first step of proposed alternative method for degradation of Cinchona alkaloids via oxidation to produce 1-azabisiklo[2.2.2]oktana.