一种改进的由氨基酸酯制备手性氨基醇的新方法.pdfVIP

538 2007 1 1,2 1 1* , , , 1. , 530001; 2. , 473058 : 采用NaBH / CeCl 作为还原体系, 在无水甲醇溶剂中, 将氨基酸甲酯还原为相应的手性氨 4 3 基醇以L苯丙氨酸甲酯还原制备L苯丙氨醇的 应为研究对象, 考察了催化剂用量 应温度 及时间诸因素对产品收率的影响结果表明: 在 n L苯丙氨酸甲酯 n CeCl3 12 应温度30 应时间2 h 的优化条件下, L苯丙氨醇收率为90. 3% 本法有操作简便, 收率高等优点, 该 应为制备手性氨基醇提供了一种新的有用的合成方法 : 氨基酸; 氨基醇; 还原:NaBH4 / CeCl3 : O 621. 25 :A : 0座机电话号码 2007 0953803 An mproved Procedure for Preparing Chiral Aminoalcohols from Aminoacid Esters 1 1, 2 1 1* GAN Chunfang , FENG Rui , FAN Jianchun , CU Jianguo 1. Department of Chemistry , Guangxi Teachers Education University, Guangxi Nanning 30001 , China; 2. Nanyang Medical College, HenanNanyang 4730 8, China Abstract : Aminoalcohols were prepared by the reduction of amino acid esters with NaBH4CeCl3 as the reducing agent in anhydrous CH3 OH. The factors affecting the synthesis, including temperature, amount of catalyst and reaction t ime, were investigated taking the reduction of methyl 3phenylalaninate as an example. The optimum conditions were as follows: molar ratio of Lmethyl phenylalaninate to CeCl , 12; reaction temperature, 30 ; and reaction t ime, 2 h. The yield 3 of 3phenyl2aminolpropanol reached 90. 3% . The method has the advantages of simple operation and higher yield. The reaction provides a useful method for the preparation of chiral aminoalcohols. Key words: aminoacid; aminoalcohol; reduction; NaBH4CeCl3 , 1 [ 1] [ 2] , 1. 1 , , , LiAlH4 [ 3] NaBH4LiCl[4] NaBH4TiCl4 [ 5] NaBH4 , Nicolet [ 6] [ 7] 1 13 CaCl2 NaBH42 , FT360 , KBr ; H C , Varian Unity nova 500 500 MHz , NaBH CeCl ; X6 4 3 , , , : 座机电话号码; : 座机电话号码 : 057554 : 1973~ , , , , * , Email: cuijg1954@ 126. com 9 539 1. 2 0. 76 g 0. 02 mol NaBH , TLC 4 1 2a2e V95% V 73 , 2 h , L 2a : 30 mL , 6 molL , 3. 30 g 0. 02 mol L, , pH 1, , , , , , , TLC , , 3a V95% V 101 , , 1. 51 g, 90. 3% , mp 91~ 92 mp 90 , ~ 92 R KBr cm- 1 : 3358, 3133, 3080, 2933, , NaHCO pH 8, 2876, 1585, 1495, 1446, 1335, 1123,