(RR)及(SS)-2-氨基-1,2-二苯基乙醇的合成  

Synthesis of(RR)and(SS)-2-amino-1,2-diphenyl Ethanol

作　　者：李林强 陈宇 赵建强 葛真真 陈明丰 陈永正 周鸣强 LI Linqiang;CHEN Yu;ZHAO Jianqiang;GE Zhenzhen;CHEN Mingfeng;CHEN Yongzheng;ZHOU Mingqiang(Key Laboratory of Biocatalysis and Chiral Drug Synthesis of Guizhou Province,College of Pharmacy,Zunyi Medical University,Zunyi 563000,China;National Engineering Research Center of Chiral Drugs,Chengdu Likai Chiral Tech Co.,Ltd.,Chengdu 610041,China;Institute for Advanced Study,Chengdu University,Chengdu 610106,China;Zhejiang Nexchem Pharmaceutical Co.,Ltd.,Jinhua 321016,China)

机构地区：[1]遵义医科大学药学院贵州省生物催化与手性药物合成重点实验室,贵州遵义563000 [2]成都丽凯手性技术有限公司手性药物国家工程研究中心,四川成都610041 [3]成都大学高等研究院,四川成都610106 [4]浙江耐司康药业有限公司,浙江金华321016

出　　处：《合成化学》2023年第7期527-532,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22171029,21901024,21871252,21801024,21801026)。

摘　　要：光学纯的2-氨基-1,2-二苯基乙醇是一类用途广泛的手性β-氨基醇,在手性药物的研发与手性配体的合成等领域有着重要的用途。分别以(RS及SR)-2-氨基-1,2-二苯基乙醇作为原料,通过6步反应,获得了手性的(RR)及(SS)-2-氨基-1,2-二苯基乙醇。反应途径主要包括Boc基团保护氨基、PCC试剂氧化羟基、Ni+H_(2)还原法还原酮羰基、乙酰基保护羟基、碱性条件脱Ac保护基团和酸性条件下脱除Boc基团。产物结构经过^(1)H NMR和^(13)C NMR分析表征。Optically pure 2-amino-1,2-diphenyl ethanol is a kind of chiral β -amino alcohols, which is widely used in the field of chiral drugs development and the synthesis of chiral ligands. In this paper, chiral( RR ) and( SS )- 2-amino-1,2-diphenyl ethanol was obtained with( RS and SR )-2-amino-1,2-diphenyl ethanol as raw material by a 6-step reaction. The reaction pathway mainly includes Boc group protecting amino group, PCC reagent oxidizing hydroxyl group, Ni+H_(2) reducing ketocarbonyl group, acetyl group protecting hydroxyl group, alkaline condition removing Ac protection group and acidic condition removing Boc group. These compounds were characterized by ^(1)H NMR and ^(13)C NMR.

关 键 词：氨基醇 PCC氧化 氢化还原 保护基 合成 工艺优化 

分 类 号：O622.3[理学—有机化学]