第 46 卷第 3 期 Vol. 46 No. 3 2016 年 6 月 Jun 2016

所属栏目：医药及中间体 （S）-1-（（4-甲酰基苯基）甲基）-5-氧代四氢吡咯-2-羧酸甲酯的合成

孙 逊，许永男，张 辉* （沈阳药科大学 制药工程学院，辽宁 沈阳 110016）

摘　要：以对羟甲基苯甲醛和三甲基氯硅烷为原料，在碘化钠催化作用下对苄位羟基进行卤代，卤化产物与L-谷氨酸二甲酯盐酸盐在碳酸钾作为缚酸剂条件下环化，得到目标产物（S）-1-（（4-甲酰基苯基）甲基）-5-氧代四氢吡咯-2-羧酸甲酯。考察了物料配比、反应温度等不同因素对反应的影响。优化条件下反应总收率为57.5%。目标化合物结构经1H NMR、13C NMR、GC-MS确证。

关键词：卤代；L-谷氨酸二甲酯盐酸盐；环化

中图分类号：TQ254.2+4　　文献标识码：A　　文章编号：1009-9212（2016）03-0042-03

Synthesis of (S)-1-((4-Formylphenyl)methyl)-5-oxo- pyrrolidine-2-carboxylate

SUN Xun, XU Yong-nan, ZHANG Hui* (College of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China)

Abstract：(S)-1-((4-Formylphenyl)methyl)-5-oxopyrrolidine-2-carboxylate was obtained using p-hydroxylbenz-aldehyde as the starting material. The typical process included the hydroxyl group on p-hydroxylbenzaldehyde was halogenated using sodium iodide and TMSC; dimethyl L-glutamate hydrochloride was added to displace the halogen by adding anhydrous potassium carbonate as acid binding agent; cyclization by adding acetic acid, the crude product was further purified by silica gel column chromatography. The main influence factors including the ratio of materials, the temperature of reaction were evaluated. The total yield of the reaction is 57.5%. The structure of this target compound was also characterized using 1H NMR, 13C NMR and GC-MS.

Key words：halogenation; dimethyl l-glutamate hydrochloride; cyclization

作者简介：孙 逊（1990-），男，辽宁铁岭人，硕士研究生，主要从事药物化学与有机化学研究。

联 系 人： 张辉，副教授，硕士生导师，主要从事药物化学与有机化学研究（E-mail：zh19683@163.com）。

收稿日期： 2016-04-2