2-氨基-5-羟基己内酰胺的合成  

Synthesis of 2-amino-5-hydroxycaprolactams

作　　者：刘起军[1,2] 李宏[1,2] 周国春[1,2] 

机构地区：[1]中国科学院广州生物医药与健康研究院,广东广州510663 [2]中国科学院研究生院,北京100039

出　　处：《化学试剂》2011年第10期867-870,共4页Chemical Reagents

基　　金：国家自然科学基金资助项目(30973621)

摘　　要：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。Olefin was prepared starting from L-gultumic acid and converted into mono-Boc protected olefin 4.Olefin 4 was epoxidized by m-CPBA and then ring opening of epoxide 5 was conducted by NaN3 under MeOH-H2O to form azide 6,at last,2-amino-5-hydroxycaprolactam was synthesized by the reduction of azide 6 using H2 with Pd/C followed by refluxing in EtOH.The diastereomeric mixture of 1 was esterified into cyclohexylformyl esters 2a and 2b,which were easily separated by silica gel column.Finally,optically pure 1a and 1b were obtained by hydrolysis of 2a and 2b,respectively.

关 键 词：2-氨基-5-羟基己内酰胺 环氧开环 环合 差向异构体 

分 类 号：O622.6[理学—有机化学]