(S)-4-羟基吡咯烷-2-酮的简便合成  

A Facile Synthesis of (S)-4-hydroxypyrrolidin-2-one

作　　者：刘洋[1] 张锋[1] 林紫云[1] 黄海洪[1] 

机构地区：[1]北京协和医学院中国医学科学院药物研究所,北京100050

出　　处：《合成化学》2010年第3期375-377,共3页Chinese Journal of Synthetic Chemistry

摘　　要：(S)-3-羟基-γ-丁内酯开环制得手性3,4-二羟基丁酸甲酯(2);对2的伯羟基进行对甲苯磺酰化、仲羟基进行苄基保护得4-对甲苯磺酰氧基-3-苄氧基丁酸甲酯(5);5在氨甲醇作用下合环、脱苄基保护合成了(S)-4-羟基吡咯烷-2-酮,总收率26%,其结构经1HNMR和HR-MS确认,比旋光值与文献值相符。The chiral diol methyl 3,4-dihydroxybutanoate（2）was prepared by ring-opening reaction of（S）-3-hydroxy-γ-butyrolactone.The primary hydroxy group of 2 was selectively tosylated first and then the key intermediate 5 was obtained via benzylation of the secondary hydroxy group in good yield.（S）-4-hydroxypyrrolidin-2-one in overall yield of 26% was synthesized by the subsequent cyclization with ammonia methanol solution of 5 and then debenzylation.The structure was confirmed by 1H NMR and HR-MS and its optical rotation was in good accordance with the reported value.

关 键 词：(S)-4-羟基吡咯烷-2-酮 对甲苯磺酰化 合环 脱苄基保护 合成 

分 类 号：O626.13[理学—有机化学]