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(S)-2-氨基-1,1-二苯基-1-丙醇的合成和外消旋Droxidopa前体的拆分
引用本文:张成刚,罗焕,匡德忠,李鸿波,李蕾蕾,王海平,秦圣英. (S)-2-氨基-1,1-二苯基-1-丙醇的合成和外消旋Droxidopa前体的拆分[J]. 化学研究与应用, 2006, 18(2): 165-168
作者姓名:张成刚  罗焕  匡德忠  李鸿波  李蕾蕾  王海平  秦圣英
作者单位:四川师范大学化学与材料科学学院,四川,成都,610066;四川倍达尔新技术开发有限公司,四川,成都,610041;四川倍达尔新技术开发有限公司,四川,成都,610041;四川大学化学学院,四川,成都,610064
摘    要:(S)-2-氨基-1,1-二苯基-1-丙醇是一种合成多种手性助剂的重要中间体,也用于外消旋屈昔多巴前体化合物的拆分。从价廉易得的L-丙氨酸出发,通过四步反应制得,总收率55.6%L-丙氨酸经甲酯化,苄氧羰基保护制得的L-2-苄羰基氨基丙酸甲酯与苯基溴化镁反应制得(S)-2-苄氧羰基氨基-1,1-二苯基-1-丙醇。是在5%Pd/C催化加氢下脱除苄氧羰基得到标题化合物。该制备方法涉及的中间体及目标化合物易于纯化,总收率高且重现性好。我们用制得的氨基醇能成功地拆分外消旋苏式屈昔多巴前体化合物3-3,4-二苄氧苯基)-N-苄氧羰基丙氨酸。

关 键 词:拆分剂  (S)-2-胺基-1  1-二苯基-1-丙醇  β-氨基醇  屈昔多巴
文章编号:1004-1656(2006)02-0165-04
收稿时间:2005-04-10
修稿时间:2005-10-12

Synthesis of (S) - - 2 - amino - 1,1 - diphenyl - 1 - propanol, a resolving reagent to racemic droxidopa Precursor
ZHANG Cheng-gang,LUO Huan,KUANG De-zhong,LI Hong-bo,LI Lei-lei,WANG Hai-ping,QIN Sheng-ying. Synthesis of (S) - - 2 - amino - 1,1 - diphenyl - 1 - propanol, a resolving reagent to racemic droxidopa Precursor[J]. Chemical Research and Application, 2006, 18(2): 165-168
Authors:ZHANG Cheng-gang  LUO Huan  KUANG De-zhong  LI Hong-bo  LI Lei-lei  WANG Hai-ping  QIN Sheng-ying
Affiliation:1. Department of Chemistry and material sciences, Sichuan Normal University, Chengdu 610066, China; 2. Department of Chemistry, Sichuan University,Chengdu 610064, China; 3. Sichan Better New Technology Development Co. ,Ltd. ,Chengdu 610041 ,China
Abstract:(S)--2-Amino-1,1-diphenyl-1-propanol(3),an important compound for many chiral catalysts and a good re-solving reagent to racemic Droxidopa precursor was prepared by 4 steps from L-alanine with total yield of 55.6%.L-2-Benzy-loxycarbonylamino-propionic acid methyl ester(1),which was obtained from L-alaninge by methy lation and benzyloxycarbonyla-tion,reacted with PhMgBr to give(S)-2-Benzyloxycarbonylamino-1,1-diphenyl-1-propanol(2).2 hydrogenolysized withH2catalyzed by 5%Pd/C to give target compond 3.3 was successfully applied to resolve rac-threo3-(3,4-dibenzyloxyphenyl)-N-carbobenzoxyserine(4)which is Droxidopa(5)precursor.This new method has good reproducibility and simple purificationprocess as well as relatively high total yield.
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