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Process for preparation of 3-carbonyl-bicyclo[2.2.2]octane-2-formate

A formate and alkoxycarbonyl ring technology, applied in the field of organic chemical synthesis of pharmaceutical intermediates, can solve the problems of difficult industrialization, low yield, and high production cost of octane-2-formate, and achieve low production cost , The effect of low equipment requirements and mild reaction conditions

Inactive Publication Date: 2020-09-22
RAFFLES PHAMRMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Based on this, it is necessary to provide a solution to this problem that can further reduce the cost of preparation of 3-carbonyl-bicyclo[2.2.2]octane-2-carboxylate. Method for preparing 3-carbonyl-bicyclo[2.2.2]octane-2-carboxylate with cost, simplification of production operation procedures, suitability for large-scale industrial production and improvement of production efficiency

Method used

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  • Process for preparation of 3-carbonyl-bicyclo[2.2.2]octane-2-formate
  • Process for preparation of 3-carbonyl-bicyclo[2.2.2]octane-2-formate
  • Process for preparation of 3-carbonyl-bicyclo[2.2.2]octane-2-formate

Examples

Experimental program
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Effect test

Embodiment 1

[0054] When X, Y are all selected from methyl, the synthetic route is:

[0055]

[0056] Concrete synthetic steps are:

[0057] Synthesis of S10.2-(4-methoxycarbonylcyclohexyl)methyl acetate

[0058] Add 500L methanol, 100.0kg 2-(4-methoxycarbonylcyclohexylene) methyl acetate, 5 kg10% palladium carbon to the reaction kettle, vacuumize the reaction kettle, replace with nitrogen, repeat three times, and then hydrogenate at normal temperature and pressure for 8 hour, filter, remove palladium carbon, obtain 2-(4-methoxycarbonylcyclohexyl) methyl acetate after the filtrate is concentrated, directly used in the next step;

[0059] Synthesis of S20.3-carbonyl-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

[0060] Add 1000L of methanol and 120kg of sodium tert-amyloxide to the above-mentioned 2-(4-methoxycarbonylcyclohexyl)methyl acetate, heat and reflux for 15 hours under nitrogen protection, drop to room temperature, and add the reaction solution into hydrochloric acid so...

Embodiment 2

[0063] When X, Y are all selected from ethyl, the synthetic route is:

[0064]

[0065] Synthesis of S10.2-(4-ethoxycarbonylcyclohexyl) ethyl acetate

[0066] Add 500L ethanol, 101.0kg 2-(4-ethoxycarbonylcyclohexylene) ethyl acetate, 5 kg5% platinum carbon to the reaction kettle, vacuumize, replace with nitrogen, repeat three times, then heat up to 40-50°C for hydrogenation reaction After 18 hours, filter to remove platinum carbon, and obtain 2-(4-methoxycarbonylcyclohexyl) ethyl acetate after the filtrate is concentrated, which is directly used in the next step;

[0067] Synthesis of S20.3-carbonyl-bicyclo[2.2.2]octane-2-ethyl carboxylate

[0068] Add 1000L ethanol, 31.6kg 20% ​​sodium ethylate solution to the above-mentioned 2-(4-ethoxycarbonylcyclohexyl) ethyl acetate, heat and reflux under nitrogen protection for 18 hours, drop to room temperature, and add the reaction solution to the hydrochloric acid solution After quenching, adding ethyl acetate for extraction, the...

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Abstract

The invention discloses a method for preparing 3-carbonyl-bicyclo[2.2.2]octane-2-formate, 2-(4-alkoxycarbonyl cyclohexylidene)acetate is used as an initial raw material, catalytic hydrogenation and condensation are sequentially performed to obtain the 3-carbonyl-bicyclo[2.2.2]octane-2-formate, and X and Y are independently selected from alkyl or aryl. According to the method, the synthetic route is short, the reaction conditions are mild, and the total yield is greater than 80%; and the method has the advantages of accessible raw materials, lower production cost and low facility request, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis of pharmaceutical intermediates, and relates to a pharmaceutical intermediate, in particular to a method for preparing 3-carbonyl-bicyclo[2.2.2]octane-2-carboxylate. Background technique [0002] 3-Carbonyl-bicyclo[2.2.2]octane-2-carboxylate is a kind of small molecule with high difficulty in synthesis. The synthetic reports of this structural fragment of ester mainly contain the following routes. [0003] This route uses cyclohexadiene as the starting material, and Diels-Alder reaction (Diels-Alder reaction) occurs with methyl 3-bromopropiolate, and further, under the action of sodium methoxide, it is substituted and added with methanol Synthesis reaction, followed by acidic hydrolysis, and finally catalytic hydrogenation under palladium catalyst conditions to obtain 3-carbonyl-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester. The main disadvantages of this route include the poor st...

Claims

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Application Information

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IPC IPC(8): C07C67/313C07C69/757C07C67/303C07C69/75C07C227/00C07C229/48
CPCC07B2200/07C07C67/303C07C67/313C07C227/00C07C2601/14C07C2602/18C07C69/757C07C69/75C07C229/48
Inventor 黄志宁叶伟平周章涛费安杰陈润林崔锦栋蓝天琪
Owner RAFFLES PHAMRMATECH CO LTD
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