Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of chiral diphenylethylenediamine ruthenium complex

A technology of diphenylethylenediamine ruthenium and complex compounds, which is applied in the directions of ruthenium organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problem of increased metal consumption, reduced product yield, low product purity, etc. problems, to achieve the effect of improving metal utilization, reducing production costs, and simple operation steps

Inactive Publication Date: 2022-05-06
浙江微通催化新材料有限公司
View PDF9 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of this, the present invention provides a preparation method of chiral diphenylethylenediamine ruthenium complex, which solves the complicated reaction preparation process of the method for obtaining the target product in the prior art, and the post-treatment cycle is long. The purity of the obtained product is also low, and the obtained product must be further recrystallized and purified, resulting in a decrease in product yield and an increase in metal consumption

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of chiral diphenylethylenediamine ruthenium complex

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0022] The invention provides a kind of preparation method of chiral diphenylethylenediamine ruthenium complex, comprising the following steps:

[0023] (a) react after mixing (1,5-cyclooctadiene) ruthenium dichloride, an organic solvent and 1,3,5-trimethylbenzene to obtain a solution system A;

[0024] (b) mixing [(1R,2R) or (1S,2S)-N-(2-amino-1,2-diphenylethyl)]p-toluenesulfonamide with an organic solvent to obtain a solution system B;

[0025] (c) react after mixing the solution system A, the solution system B and the alkali reagent, after the reaction is completed, sequentially cool, filter, wash, drain, and vacuum-dry to obtain the chiral diphenylethylenediamine ruthenium complex;

[0026] The chiral diphenylethylenediamine ruthenium complex is {[(1R, 2R) or (1S, 2S)-(-)-2-amino-1,2-diphenylethyl] (p-toluene Sulfonyl)amino}(mesitylene)ruthenium chloride.

[0027] In the present invention, the reactions in the steps (a), (b) and (c) are independently carried out in an ox...

Embodiment 1

[0043] (a) Mix 14.01g (1,5-cyclooctadiene) ruthenium dichloride and 60mL absolute ethanol at 65°C in an oxygen-free atmosphere, then add 24.04g of 1,3,5-tri Toluene was stirred and reacted for 5h to obtain solution system A;

[0044] (b) Mix 19.30g of the ligand (1R,2R)-N-(2-amino-1,2-diphenylethyl)p-toluenesulfonamide and 60mL of petroleum ether at room temperature under oxygen-free conditions, and stir until clarified to obtain solution system B;

[0045] (c) Under stirring and anaerobic state, add 20.51 g of anhydrous sodium acetate to the solution system A obtained in step (a), stir for 5 minutes to obtain a mixed solution, and then add solution system B obtained in step (b) dropwise Add it to the mixture, add it dropwise for 10 minutes, and continue to stir and react for 3 hours at 65°C. After the reaction is complete, cool, filter, wash, and dry it, and dry it in vacuum at 60°C for 5 hours to obtain 28.40 g of the target product. The yield is 91.3%, and the product pur...

Embodiment 2

[0048] (a) Mix 14.01g (1,5-cyclooctadiene) ruthenium dichloride and 90mL isopropanol at 75°C in an oxygen-free atmosphere, then add 30.14g of 1,3,5-tri Toluene was stirred and reacted for 4h to obtain solution system A;

[0049] (b) At room temperature and under anaerobic conditions, mix 20.14g of ligand (1S,2S)-N-(2-amino-1,2-diphenylethyl)p-toluenesulfonamide and 150mL of cyclohexane, and stir To clarification, obtain solution system B;

[0050] (c) Under stirring and anaerobic state, add 26.51 g of anhydrous sodium acetate to the solution system A obtained in step (a), stir for 15 minutes to obtain a mixed solution, and then add the solution system B obtained in step (b) dropwise Add to the mixture, add dropwise for 15 minutes, and continue to stir and react for 2.5 hours at 75°C. After the reaction is complete, cool, filter, wash, dry, and vacuum dry at 70°C for 4 hours to obtain 28.19g of the target product , yield 90.6%, product purity 98.7%.

[0051] The elemental an...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of preparation of ruthenium noble metal catalysts in the fields of medicine synthesis, pesticides, fine chemical engineering and the like, and discloses a preparation method of a chiral diphenyl ethylenediamine ruthenium complex {[(1R, 2R) or (1S, 2S)-(-)-2-amino-1, 2-diphenyl ethyl] (p-toluenesulfonyl) amino} (mesitylene) ruthenium chloride. According to the method, the target product is obtained through one-step synthesis reaction through adjustment of the alkali reagent under the anaerobic condition and the mixed solvent system, the overall operation steps are simple and convenient, the synthesis period is short, the production efficiency is improved, the yield of the target product reaches 90.0% or above, and the purity is larger than 98.5%.

Description

technical field [0001] The invention relates to the technical field of preparation of ruthenium noble metal catalysts in the fields of pharmaceutical synthesis, pesticides, fine chemicals and the like, and in particular to a preparation method of chiral diphenylethylenediamine ruthenium complex. Background technique [0002] Chiral ligands and chiral catalysts are the core of the field of chiral catalytic synthesis, which are widely used in the production of medicine, liquid crystal materials, agrochemical and fine chemical industries. At this stage, {[(1R,2R) or (1S,2S)-(-)-2-amino-1,2-diphenylethyl](p-toluenesulfonyl)amino)}(mesitylene)chloride Ruthenium complexes have made great breakthroughs in the field of specific asymmetric catalysis, and are widely used in the asymmetric catalytic hydrogenation of ketones and imines, Michael reaction, Diels-Alder reaction, Henry reaction, etc. Compared with small-molecule chiral diamine catalysts, chiral diamine-coordinated metal ru...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F15/00
CPCC07F15/0046C07B2200/07
Inventor 黄鹏陈华刘斌李珊珊尹登科杨立强李志远王惟魏青谢智平鞠景禧
Owner 浙江微通催化新材料有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com