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以L-谷氨酸为起始原料,中间体的末端双键环氧化后在甲醇-水体系中利用叠氮化钠对环氧开环形成叠氮化合物,叠氮化合物被还原为胺后在回流条件下直接环合形成非对映异构体(2S,5S)-2-氨基-5-羟基己内酰胺和(2S,5R)-2-氨基-5-羟基己内酰胺的混合物,该混合物的5-羟基被环己基甲酰基酯化后形成的环己基甲酰基酯可以通过硅胶柱分离得到光学纯的环己基甲酰基酯。进一步将环己基甲酰基水解后分别得到光学纯的(2S,5S)-异构体和光学纯的(2S,5R)-异构体。
Starting from L-glutamic acid, after the terminal double bond of the intermediate is epoxidized, the azide is ring-opened by sodium azide in a methanol-water system to form an azide, and the azide is reduced to an amine A mixture of diastereomer (2S, 5S) -2-amino-5-hydroxycaprolactam and (2S, 5R) -2-amino-5- hydroxycaprolactam was directly cyclized under reflux conditions with a mixture of 5 - The cyclohexyl formyl ester formed by the esterification of a hydroxyl group with a cyclohexyl formyl group can be separated by a silica gel column to obtain an optically pure cyclohexyl formyl ester. Further hydrolysis of the cyclohexylformyl group gave the optically pure (2S, 5S) -isomer and the optically pure (2S, 5R) -isomer, respectively.