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

Method for directionally synthesizing (4-chlorphenyl)-(pyridine-2-base)-methanol

A technology for directional synthesis and compound, applied in the direction of organic chemistry, etc., can solve the problems of many steps, complicated operation and high cost, and achieve the effects of mild reaction conditions, simple and easy method, and high product yield.

Inactive Publication Date: 2013-05-29
CHONGQING HUABANGSHENGKAI PHARM
View PDF2 Cites 20 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the precious metal ruthenium ligand in method 1 is difficult to purchase, the cost is high, and high pressure reaction is required, which limits industrial production;
[0009] Method 2 has many steps and is cumbersome to operate, which is also unfavorable for industrialized 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
  • Method for directionally synthesizing (4-chlorphenyl)-(pyridine-2-base)-methanol
  • Method for directionally synthesizing (4-chlorphenyl)-(pyridine-2-base)-methanol
  • Method for directionally synthesizing (4-chlorphenyl)-(pyridine-2-base)-methanol

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0032] 2. The preparation method of chiral reducing agent BINAL-H is as follows:

[0033]

[0034] 3. The purity of the chiral product in R or S configuration (4-chlorophenyl)-(pyridin-2-yl)-methanol is determined by HPLC, and detected by a chiral chromatographic column. The detection conditions are as follows:

[0035] Testing instrument: LC-10ATVP

[0036] Chromatographic column: chiral column Chiral OD (Daicel)

[0037] Mobile phase: hexane-ethanol (95:5)

[0038] Detection wavelength: 254nm

[0039] Injection concentration and volume: 100ug / ml, 20ul

[0040] Column temperature: 35°C

[0041] Flow rate: 0.75ml / min

Embodiment 1

[0043] Take 87.6g (0.4mol) of (4-chlorophenyl)-(pyridin-2-yl)-methanone (Formula II), dissolve it in 200mL of dichloromethane, and add it dropwise to In 1000mL of dichloromethane containing 0.8mol (S)-BINAL-H, keep the reaction at -100~-80°C, and detect the end point of the reaction by thin-layer chromatography (the developing solvent is methanol: chloroform: acetic acid 7: 2: 1 ). After the reaction is complete, add 300 mL of ethanol to the reaction solution, adjust the pH to 4.5-5.5 with 1N hydrochloric acid, add 500 mL of saturated saline, extract with ether, dry the extract with magnesium sulfate, concentrate, and recrystallize with ethyl acetate-petroleum ether. 63.3 g of (S)-(4-chlorophenyl)-(pyridin-2-yl)-methanol was obtained, with a yield of 72.3% and a purity of 86.2%.

Embodiment 2

[0045] Take 87.6 g (0.4 mol) of (4-chlorophenyl)-(pyridin-2-yl)-methanone (Formula II), dissolve it in 200 mL of ether, and add it dropwise to 3.2 mol(R)-BINAL-H in 1000mL ether solution, kept at -60~-50°C for reaction, and detected the end point of the reaction by thin-layer chromatography (developing solvent: methanol: chloroform: acetic acid 7:2:1). After the reaction is complete, add 500 mL of methanol to the reaction solution, adjust the pH to 4.5-5.5 with 1N hydrochloric acid, add 500 mL of saturated saline, extract with ether, dry the extract with magnesium sulfate, concentrate, and recrystallize with ethyl acetate-petroleum ether. 72.8 g of (R)-(4-chlorophenyl)-(pyridin-2-yl)-methanol was obtained, with a yield of 82.3% and a purity of 95.7%.

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

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention relates to a method for directionally synthesizing a compound which is shown in a formula I and has a single structure through taking a compound in a formula II as a raw material. The method is characterized in that the compound in the formula II is subjected to reduction reaction through a chiral reducing agent-BINAL-H. By utilizing the method, the target product with the single structure can be obtained through one step of reaction under the condition of normal pressure, the product content can reach 95%, and the yield can reach 82%. The method is simple and practicable and has a high industrial application value.

Description

Technical field: [0001] The invention relates to a method for directional synthesis of chiral compounds, in particular to using (4-chlorophenyl)-(pyridin-2-yl)-methanone as a raw material for directional synthesis of (4-chlorobenzene base)-(pyridin-2-yl)-methanol method. Background technique: [0002] The chiral compound (4-chlorophenyl)-(pyridin-2-yl)-methanol (formula I) has two configurations of S and R, and is an important intermediate in the pharmaceutical industry, such as (S)-( 4-Chlorophenyl)-(pyridin-2-yl)-methanol can be used to synthesize the antiallergic drug bepotastine. [0003] With (4-chlorophenyl)-(pyridin-2-yl)-methanone (formula II) as raw material, the method of reducing carbonyl can be used to synthesize single-configuration (4-chlorophenyl)-(pyridine- 2-yl)-methanol. [0004] [0005] In the prior art, there are mainly the following two methods to realize: [0006] 1. With (4-chlorophenyl)-(pyridin-2-yl)-methanone (formula II) as raw material, (S...

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 Applications(China)
IPC IPC(8): C07D213/30
Inventor 陈小舟
Owner CHONGQING HUABANGSHENGKAI PHARM
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