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CN102731389A 一种（R）/（S）-6,6’-二羟基-5,5’-双喹啉的合成方法 失效 - 权利终止

一种（R）/（S）-6,6’-二羟基-5,5’-双喹啉的合成方法
摘要：
本发明涉及双喹啉的合成方法，具体涉及一种（R）/（S）-6,6’-二羟基-5,5’-双喹啉的合成方法，该方法由以下步骤组成：将6-羟基喹啉加入含有二氯化铜和有机胺的甲醇溶液中氧化偶联得到的外消旋6,6’-二羟基-5,5’-双喹啉与D-(+)-樟脑磺酰氯反应得到6,6’-二羟基-5,5’-双喹啉二樟脑磺酸酯，再将6,6’-二羟基-5,5’-双喹啉二樟脑磺酸酯分别在由乙酸乙酯、甲醇与正己烷组成的混合溶剂中结晶得到（R）/（S）-6,6’-二羟基-5,5’-双喹啉二樟脑磺酸酯；然后，将（R）/（S）-6,6’-二羟基-5,5’-双喹啉二樟脑磺酸酯在碱性条件分别水解得到（R）/（S）-6,6’-二羟基-5,5’-双喹啉。本发明所述的合成方法不需要采用手性柱分离，具有操作简单方便、拆分产率高的优点。
摘要（英）：

The invention relates to a synthesis method of biquinoline, in particular to a synthesis method of (R)/(S)-6,6'-benzyloxyl-5,5'-biquinoline. The synthesis method comprises the following steps of: adding 6-hydroxyquinoline to a methanol solution containing copric chloride and organic amine to oxidize and couple to obtain racemization 6,6'-benzyloxyl-5,5'-biquinoline, and carrying out a reaction onthe racemization 6,6'-benzyloxyl-5,5'-biquinoline and D-(+)-camphorsulfonyl chloride to obtain 6,6'-benzyloxyl-5,5'-biquinoline dicamphor sulfonic acid ester; crystallizing the 6,6'-benzyloxyl-5,5'-biquinoline dicamphor sulfonic acid ester in a mixed solvent containing ethyl acetate, methanol and normal hexane to obtain (R)/(S)-6,6'-benzyloxyl-5,5'-biquinoline dicamphor sulfonic acid ester; and then hydrolyzing the (R)/(S)-6,6'-benzyloxyl-5,5'-biquinoline dicamphor sulfonic acid ester to obtain the (R)/(S)-6,6'-benzyloxyl-5,5'-biquinoline. Chiral column separation is not needed by the synthesis method provided by the invention, and the synthesis method has the advantages of simplicity and convenience for operations and high split yield.

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