Corey内酯中间体2-氧代三环[2.2.1.0^(3,5)]庚烷-7-羧酸的新拆分方法

New optical resolution of 2-oxotricyclo[2.2.1.0^(3,5)] heptanes-7-carboylic acid as an intermediate of Corey lactones

光学纯2-氧代三环[2.2.1.03,5]庚烷-7-羧酸是全合成前列腺素类化合物的重要中间体。本文采用(S)-(-)-N-苄基苯-α-苯乙胺为手性拆分剂,以醋酸异丙酯为溶剂,以非对映异构体结晶法制备光学纯(+)-2-氧代三环[2.2.1.03,5]庚烷-7-羧酸。本方法成功完成了消旋体酸(70 g)的拆分,总收率57%,所得产品对映体过量(e.e.)大于99%。本方法操作简便,收率高,溶剂及手性胺可回收。

A practical method for the resolution of racemic 2-oxotricyclo[2.2.1.03,5]heptanes-7-carboylic acid has been developed,which employs（S）-（-）-N-benzyl-α-methylbenzylamine as the resolving agent and isopropyl acetate as the solvent.This new process has been successfully implemented on resolving 70 gram racemic acid with satisfying yield（57%） and high enantiomeric excess（e.e.）value（99%）.The chiral base and the solvent could be easily recovered and recycled.