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Method for preparing dolasetron mesylate key intermediate based on graphene activation

A technology of dolasetron mesylate and graphene, which is applied in organic chemistry and other fields, can solve problems such as a large impact on yield, achieve good antibacterial properties, high specific surface area, and improve reaction efficiency and activity.

Inactive Publication Date: 2018-12-11
武汉军嘉特商贸有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Known by above-mentioned prior art, dolasetron mesilate can further improve the effect of dolasetron mesilate by hydrolysis recrystallization and adding auxiliary agent, but the output of dolasetron mesilate is affected by (2α, 6α , 8α, 9αβ)-hexahydro-8-hydroxyl-2,6-methylene-2H-quinolin-3(4H)-one intermediate has a greater impact on the yield

Method used

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  • Method for preparing dolasetron mesylate key intermediate based on graphene activation

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) According to the mass ratio of methyl 3-cyclopentene-1-carboxylate and N-methylmorpholine-N-oxide, potassium osmate, phenylboronic acid and sodium periodate is 1:0.1:0.05:0.05 : 0.3,3-cyclopentene-1-carboxylic acid methyl ester in the aqueous solution of N-methylmorpholine-N-oxide, after mixing evenly, first add potassium osmate and phenylboronic acid, and oxidize at 0°C for 15 minutes Afterwards, add sodium periodate again, and continue to heat up to 10°C at a rate of 1°C / min for 30 minutes of oxidation reaction to obtain CHOCH 2 -C-(COOCH 3 )-CH 2 CHO dialdehyde intermediate.

[0024] (2) Prepare 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester by reacting dialdehyde intermediate product with 1,3-acetone dicarboxylic acid by Robinson-Schoepf .

[0025] (3) According to the mass ratio of 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester and graphene oxide is 1:0.01, 3-methoxycarboxy-7 - In the tetrahydrofuran solution o...

Embodiment 2

[0027] (1) According to the mass ratio of methyl 3-cyclopentene-1-carboxylate to N-methylmorpholine-N-oxide, potassium osmate, phenylboronic acid and sodium periodate is 1:0.15:0.1:0.1 : 0.5, 3-cyclopentene-1-methyl carboxylate in the aqueous solution of N-methylmorpholine-N-oxide, after mixing evenly, first add potassium osmate and phenylboronic acid, and oxidize at 15°C for 60 minutes After that, sodium periodate was added, and the temperature was raised to 25°C for 45min at a rate of 3°C / min to obtain CHOCH 2 -C-(COOCH 3 )-CH 2 CHO dialdehyde intermediate.

[0028] (2) Prepare 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester by reacting dialdehyde intermediate product with 1,3-acetone dicarboxylic acid by Robinson-Schoepf .

[0029] (3) According to the mass ratio of 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester and graphene oxide is 1:0.1, 3-methoxycarboxy-7 - In the tetrahydrofuran solution of oxo-9-azabicyclo-nonane-9-aceti...

Embodiment 3

[0031] (1) According to the mass ratio of methyl 3-cyclopentene-1-carboxylate and N-methylmorpholine-N-oxide, potassium osmate, phenylboronic acid and sodium periodate is 1:0.12:0.06:0.08 : 0.4,3-cyclopentene-1-methyl carboxylate in the aqueous solution of N-methylmorpholine-N-oxide, after mixing evenly, first add potassium osmate and phenylboronic acid, and oxidize at 5°C for 30 minutes Afterwards, add sodium periodate again, continue to heat up to 15 ℃ oxidation reaction 35min at the rate of 2 ℃ / min, obtain CHOCH 2 -C-(COOCH 3 )-CH 2 CHO dialdehyde intermediate.

[0032] (2) Prepare 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester by reacting dialdehyde intermediate product with 1,3-acetone dicarboxylic acid by Robinson-Schoepf .

[0033] (3) According to the mass ratio of 3-methoxycarboxy-7-oxo-9-azabicyclo-nonane-9-acetic acid methyl ester and graphene oxide is 1:0.05, 3-methoxycarboxy-7 - In the tetrahydrofuran solution of oxo-9-azabicyclo-nonane...

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Abstract

The invention provides a method for preparing a dolasetron mesylate key intermediate based on graphene activation. The method comprises the following steps: after uniformly mixing 3-cyclopentene-1-methyl formate in a water solution of N-methylmorpholine-N-oxide; adding potassium osmate and phenylboronic acid; after carrying out oxidization reaction, adding sodium periodate; continually carrying out oxidization reaction to obtain a dialdehyde intermediate product; enabling the dialdehyde intermediate product and 1,3-acetonedicarboxylic acid to subjected to Robinson-Schoepf reaction to prepare 3-methoxycarboxyl-7-oxo-9-azabicyclo-nonane-9-methyl acetate; adding a graphene oxide solution into a tetrahydrofuran solution of the 3-methoxycarboxyl-7-oxo-9-azabicyclo-nonane-9-methyl acetate; afteruniformly mixing, carrying out reduction reaction on sodium borohydride and sodium iodide; adding dihydropyran; and carrying out cyclization reaction to obtain a graphene modified (2alpha,6alpha,8alpha,9alphabeta)-hexahydro-8-hydroxyl-2,6-methylene-2H-quinoline-3(4H)-one intermediate.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing a key intermediate of dolasetron mesylate based on graphene activation. Background technique [0002] 5-Hydroxytryptamine, also known as 5-HT, is an indoleethylamine, one of the most widely distributed neurotransmitters in the human body, controlling the body's appetite, body temperature, blood pressure, sleep, hobbies, pain, vomiting and other feelings. 5-HT3 receptor antagonists have a good therapeutic effect in controlling the nausea and vomiting caused by the treatment of tumors, and are one of the main ways to control vomiting and improve the quality of life of chemotherapy patients. current 5-HT 3 Receptor antagonists include ondansetron, granisetron, tropisetron, azasetron, ramosetron, dolasetron, alosetron, palonosetron, etc., of which dolase Joan's antiemetic effect is better than other 5-HT 3 Receptor antagonists are more effectiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/18
CPCC07D471/18
Inventor 陈东进
Owner 武汉军嘉特商贸有限公司
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