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Bicyclol preparation method and intermediate compound thereof

A compound and mixture technology, applied in the field of organic compound synthesis, can solve the problems of low total yield and high production cost

Active Publication Date: 2016-12-21
ZHEJIANG AUSUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Therefore, in summary, the current industrial production of bicyclic alcohols is mainly based on biphenyl diester as a raw material, which is prepared through the alcoholysis of biphenyl lactone and the selective reduction of biphenyl dioic acid monomethyl ester respectively. The main problem is the low overall yield and high production cost

Method used

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  • Bicyclol preparation method and intermediate compound thereof
  • Bicyclol preparation method and intermediate compound thereof
  • Bicyclol preparation method and intermediate compound thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: 7,7'-dimethoxy 5'-(2-thiothiazoline-3-carbonyl)-[4,4']bis[benzo[1,3]dioxolane ]-5-formic acid methyl ester (formula (4) compound, wherein R 1 , R 2 , R 3 Respectively is the preparation of methyl)

[0091] (1) 5'-chlorocarbonyl-7,7'-dimethoxy-[4,4']bis[benzo[1,3]dioxolane]-5-methyl carboxylate (formula ( 3) compound, wherein R 1 , R 2 , R 3 respectively methyl)

[0092]

[0093] 2.0 grams (5 mmol) of monomethyl biphenyl diacid (compound 2) was dissolved in 20 ml of dichloromethane, 1.5 ml (20.8 mmol) of thionyl chloride and 1 drop of dimethylformamide were added, heated to reflux for 2 hours, evaporated After drying, 2.15 g of the title product was obtained, which was directly used in the next reaction.

[0094] (2) 7,7'-dimethoxy 5'-(2-thiothiazoline-3-carbonyl)-[4,4']bis[benzo[1,3]dioxolane] -Methyl 5-formate (compound of formula (4), wherein R 1 , R 2 , R 3 Respectively is the preparation of methyl)

[0095]

[0096] Dissolve 2.1g (~5mmo...

Embodiment 2

[0098] Example 2: 4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2-hydroxymethyl-2'-methoxycarbonylbiphenyl (formula ( 1) compound, wherein R 1 , R 2 , R 3 are respectively the preparation of methyl);

[0099]

[0100] Dissolve 500 mg (1 mmol) of compound 4 in 5 ml of tetrahydrofuran, cool in an ice bath, and add dropwise a solution of 95 mg (2.5 mmol) of sodium borohydride and 0.2 ml of water in 5 ml of tetrahydrofuran under stirring at a controlled temperature of 0-5°C. After the addition, keep warm at 0-5°C and stir for 30 minutes, then raise the temperature to 30-35°C and stir for 30 minutes. The reaction solution turns from yellow to colorless, and TLC shows that the raw material spots disappear. Then dilute hydrochloric acid was added to remove excess sodium borohydride, tetrahydrofuran was evaporated under reduced pressure, the residue was dissolved in dichloromethane, followed by 5% Na 2 CO 3 Wash, wash with water, anhydrous Na 2 SO 4 dry. After filtration, th...

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Abstract

The invention relates to a bicyclol preparation method and an intermediate compound thereof. Concretely speaking, the invention relates to the preparation method of bicyclol which is 4,4'-dimethoxy-5,6,5',6'-bis(methy-lenedioxy)-2-hydroxymethyl-2'-methoxycarbonyl-biphenyl shown in a formula (1), and the intermediate compound thereof.

Description

technical field [0001] The present invention relates to the synthesis of organic compounds. Specifically, the present invention relates to the preparation method of bicyclic alcohol and its intermediate compound. Background technique [0002] The present invention relates to bicyclic alcohols, namely 4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2-hydroxymethyl-2'-methoxycarbonylbiphenyl The preparation method of the compound can be used for auxiliary treatment of chronic liver disease. [0003] Bicyclol (Bicyclol, see the formula below), the chemical name is 4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2-hydroxymethyl-2' - Methoxycarbonyl biphenyl, which has obvious protective effect on acute liver injury in mice caused by carbon tetrachloride, D-galactosamine and acetaminophen, and can reduce the increase of transaminases caused by acute liver injury in these animals , and can reduce liver tissue damage, and is now clinically used as an adjuvant treatment for chronic liv...

Claims

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Application Information

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IPC IPC(8): C07D317/68C07D417/14
CPCC07D317/68C07D417/14
Inventor 周日保徐晓荣刘瑜张曙梅邹丽玲
Owner ZHEJIANG AUSUN PHARMA
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