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

Preparation method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane

A technology of methoxyphenyl and phenylphosphino, which is applied in the field of chirality 1, can solve the problems of complex preparation process, high cost, and long route steps, and achieve high reaction efficiency, reduced production cost, and short reaction path Effect

Active Publication Date: 2022-04-05
JIANGSU SINOCOMPOUND CATALYST
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

S-butyllithium is a highly dangerous raw material, and the chiral (2-methoxyphenyl) (methyl) (phenyl) phosphine oxide preparation process of the raw material is more complicated and the cost is higher; conducive to industrial production

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 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane
  • Preparation method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane
  • Preparation method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of (R,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane:

[0035] Step 1: Under an argon atmosphere, add (2-methoxyphenyl) (methyl) (phenyl) phosphine oxide (246 g, 1.0 mol) and 2 L of tetrahydrofuran to the reactor; Add 2.5M n-butyllithium solution (0.42L, 1.05mol) dropwise into the reactor, then add anhydrous copper chloride (134g, 1.0mol) at -20°C in one go, then raise the temperature to normal temperature for reaction, filter Washing, separating and concentrating to obtain 201 g of 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide racemate with a yield of 82 %, the liquid phase chemical purity is 98.3% after detection;

[0036] Step 2: Add 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide prepared by step 1 to the reactor Racemate (150g, 0.3mol), then add methanol 450ml in the reactor, make it dissolve in methanol; Then add L-(+)-dibenzoyltartaric acid (107g, 0.3mol) and heat to reflux reaction, Then cool and fil...

Embodiment 2

[0040] Synthesis of (R,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane:

[0041] Step 1: Under an argon atmosphere, add (2-methoxyphenyl) (methyl) (phenyl) phosphine oxide (296 g, 1.2 mol) and 2 L of tetrahydrofuran to the reactor; Add 2.5M n-butyllithium solution (0.50L, 1.26mol) dropwise into the container, then add anhydrous copper chloride (161g, 1.2mol) at 0°C in one go, then heat up to normal temperature for reaction, filter and wash with water The liquid was concentrated to obtain 229 g of 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide racemate, with a yield of 78%. The tested liquid phase chemical purity is 97.8%;

[0042] Step 2: Add 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide prepared by step 1 to the reactor Racemate (150g, 0.3mol), then add methanol 450ml in the reactor, make it dissolve in methanol; Then add L-(+)-dibenzoyltartaric acid (107g, 0.3mol) and heat to reflux reaction, Then cool and filter to obtain...

Embodiment 3

[0046] Synthesis of (R,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane:

[0047] Step 1: Under an argon atmosphere, add (2-methoxyphenyl) (methyl) (phenyl) phosphine oxide (296 g, 1.2 mol) and 2 L of tetrahydrofuran to the reactor; Add 2.5M n-butyllithium solution (0.50L, 1.26mol) dropwise into the reactor, then add anhydrous copper bromide (268g, 1.2mol) at -20°C in one go, then raise the temperature to normal temperature for reaction, filter Washing, separating and concentrating gave 191 g of 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide racemate with a yield of 65 %, the liquid phase chemical purity is 96.9% after detection;

[0048] Step 2: Add 1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide prepared by step 1 to the reactor Racemate (150g, 0.3mol), then add methanol 450ml in the reactor, make it dissolve in methanol; Then add L-(+)-dibenzoyltartaric acid (107g, 0.3mol) and heat to reflux reaction, Then cool and filter to...

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

A preparation method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane belongs to the technical field of organic chemistry. The preparation method is carried out according to the following reaction paths: the present invention has short reaction paths, high reaction efficiency, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a technique in the field of organic chemistry, in particular to a preparation method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane. Background technique [0002] Chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane is as a kind of chiral phosphine ligand, and rhodium complexation forms catalyst to have extensive application in chemical industry field, and in rhodium In the catalytic asymmetric hydrogenation reaction, especially the asymmetric hydrogenation of enamine, this ligand shows remarkable activity and selectivity compared with other similar compounds. This technology has become the commercial production of amino acid 1-DOPA (3, 4-dihydroxyphenylalanine), a drug used to treat Parkinson's disease. [0003] The synthetic method of chiral 1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane reported in literature is mainly through chiral (2-methoxyphenyl)(methyl) (Phenyl) phosphine oxide is reduced with trichloro...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50
CPCC07F9/5022C07F9/509C07F9/5095C07B2200/07
Inventor 孙明明
Owner JIANGSU SINOCOMPOUND CATALYST
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