An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors

被引：9
|
作者：
Wang, Xin [1 ]
Ma, Mingliang [1 ]
Reddy, Alavala Gopi Krishna [1 ]
Hu, Wenhao [1 ]
机构：
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Dept Chem, Shanghai 200062, Peoples R China
来源：
TETRAHEDRON | 2017年 / 73卷 / 11期
关键词：
Factor Xa inhibitor; Stereoselective synthesis; 3,4-Diaminocyclohexane carboxamide; Gram scale synthesis; PHOSPHORIC-ACID; DERIVATIVES; SELECTIVITY; ESTERS;
D O I：
10.1016/j.tet.2017.01.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the title compounds was controlled at C2 center by Mitsunobu reaction and at C5 via a base-catalyzed epimerization. Only a limited usage of column chromatography has provided a direct and scalable route for the six stereoisomers. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1381 / 1388
页数：8
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