Method for preparing (+/-)-2-azabicyclo[2, 2, 1]hepta-5-alkene-3-ketone

A technology of azabicyclo and aqueous solution, applied in the direction of organic chemistry, etc., to achieve the effect of advanced technology, good product quality, and cheap and easy-to-obtain raw materials

Active Publication Date: 2016-11-16
营口昌成新材料科技有限公司
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  • Abstract
  • Description
  • Claims
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  • Method for preparing (+/-)-2-azabicyclo[2, 2, 1]hepta-5-alkene-3-ketone

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Embodiment 1

[0017] 1) Preparation of sodium methylsulfinate aqueous solution:

[0018] At room temperature, add 85.8g of water to a 500ml glass four-necked bottle (hereinafter referred to as the reaction kettle), and add 85.8g of water and an aqueous solution composed of 23.2g of sodium acetate trihydrate, then add 11.3g of sodium sulfite to the aqueous solution of sodium acetate; start stirring until the solids are completely use a low-temperature bath to cool the material in the reactor, control the temperature of the material at 5-10°C, and add 9.7g of methanesulfonyl chloride dropwise to the reactor; after the addition, continue the reaction at 10±2°C for 2 hours. An aqueous solution of sodium methanesulfinate was obtained and set aside.

[0019] 2) Preparation of (±)-2-azabicyclo[2,2,1]hept-5-en-3-one:

[0020] Control the temperature of the sodium methylsulfinate aqueous solution obtained in 1) at 8-12° C., take 100 g of dichloromethane and 40 g of cyclopentadiene monomer, and mix ...

Embodiment 2

[0022] 1) Preparation of sodium methylsulfinate aqueous solution:

[0023] At room temperature, add 85g of water and 25g of an aqueous solution of sodium acetate to a 500ml glass four-necked bottle (hereinafter referred to as the reaction kettle), and then add 12.4g of sodium sulfite; start stirring until the solids are completely dissolved; cool in a low-temperature bath For the material in the reaction kettle, control the temperature of the material at 5-10°C, and add 10.2g of methanesulfonyl chloride dropwise into the reaction kettle; after the dropwise addition, continue to react for 2 hours at the temperature of the kettle at 10±2°C to obtain methylsulfinic acid Sodium aqueous solution; the sodium methylsulfinate aqueous solution is used in the next step.

[0024] 2) Preparation of (±)-2-azabicyclo[2,2,1]hept-5-en-3-one:

[0025] Control the temperature of the sodium methylsulfinate aqueous solution obtained in 1) at 8-12°C, and add a solution consisting of 100g of chlor...

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Abstract

The invention relates to a method for preparing (+/-)-2-azabicyclo[2, 2, 1]hepta-5-alkene-3-ketone. The method includes: using sodium sulfite and methyl sulfonyl chloride in the aqueous solution of sodium acetate to generate sodium methanesulfinate, adding fixed-quantity halogenated hydrocarbon solvent and cyclopentadiene monomer, dropwisely adding the solution formed by cyanogen chloride monomer and halogenated hydrocarbon into reaction liquid, using sodium acetate aqueous solution to regulate the pH of the reaction system so as to allow the pH to be in a specific range, and extracting, regulating pH and concentrating after the reaction to obtain the (+/-)-2-azabicyclo[2, 2, 1]hepta-5-alkene-3-ketone with the purify not smaller than 98% and yield not smaller than 94%. The method is good in product quality, high in yield, low in raw material cost, simple in process, easy to operate, and the like, so that the method has better economic advantages and high competiveness in industrial production.

Description

technical field [0001] The present invention relates to a method for preparing (±)-2-azabicyclo[2,2,1]hept-5-en-3-one. Background technique [0002] (±)-2-Azabicyclo[2,2,1]hept-5-en-3-one is one of the most important raw materials or intermediates for the synthesis of anti-AIDS drug-abacavir. In recent years, there are many domestic literatures and patents on the preparation of such raw materials or intermediates. For example, patent CN101121690A has described a kind of 2-sulfinic acid base benzoic acid disodium salt with 2-sulfobenzoic anhydride and reducing agent reaction in alkaline solvent, then directly add cyclopentadiene, pass into cyanogen chloride gas , the reaction gives (±)-2-azabicyclo[2,2,1]hept-5-en-3-one; there are also documents such as "Fine Chemical Intermediates" 2006, 36(5), 36-38 describe Directly use sodium p-toluene sulfinate as a catalyst, add cyclopentadiene to a mixed solution of water and methylene chloride, feed cyanogen chloride gas, and react ...

Claims

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Application Information

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IPC IPC(8): C07D209/52
CPCC07D209/52
Inventor 杨国民贺从主贾有朋李金玉刘禹
Owner 营口昌成新材料科技有限公司
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