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Preparing method for 1,1-cyclopropyl dimethyl carbinol

A technology of cyclopropyl dimethanol and diethyl cyclopropyl dicarboxylate, which is applied in the field of pharmaceutical synthesis, can solve the problems of harsh reaction conditions, low environmental friendliness and high production cost, and achieves easy, active and cheap products, and high cost low effect

Active Publication Date: 2017-04-26
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0010] Aiming at the technical problems of high raw material toxicity, harsh reaction conditions, high production cost, low environmental friendliness and low yield in the preparation method of 1,1-cyclopropyldimethanol in the prior art, the present invention aims to provide a raw material Cheap, easy to obtain, non-toxic, mild and controllable reaction conditions, high environmental friendliness, and a method for preparing 1,1-cyclopropyldimethanol with significantly improved product yield

Method used

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  • Preparing method for 1,1-cyclopropyl dimethyl carbinol
  • Preparing method for 1,1-cyclopropyl dimethyl carbinol
  • Preparing method for 1,1-cyclopropyl dimethyl carbinol

Examples

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Embodiment 1

[0038] Example 1: Preparation of 1,1-cyclopropyldimethanol.

[0039] Add 40g (249.73mmol) of diethyl malonate, 32.14g (324.65mmol) of 1,2-dichloroethane, 3.75g (24.97mmol) of sodium iodide, DMF into a four-necked flask equipped with a mechanical stirring device. 200 mL and 75.93 g (549.41 mmol) of anhydrous potassium carbonate, the reaction system was heated to reflux under stirring conditions, the progress of the reaction was monitored by GC, and the disappearance of diethyl malonate was regarded as the end of the reaction. After the reaction, the reaction solution was cooled to room temperature and filtered. The filter cake was washed with DMF. After combining the filtrate and washing solution, the DMF was evaporated under normal pressure (recoverable and applied) to obtain crude diethyl 1,1-cyclopropyldicarboxylate 42 g (93% yield). The crude product can be used directly in the next reaction without further purification.

[0040] Add 42 g (225.56 mmol) of crude 1,1-cyclopropyl...

Embodiment 2

[0043] Example 2: Preparation of 1,1-cyclopropyldimethanol.

[0044] Into a four-necked flask equipped with a mechanical stirring device was added 40g (249.73mmol) of diethyl malonate, 27.20g (274.70mmol) of 1,2-dichloroethane, 2.07g (12.49mmol) of potassium iodide, 240mL of THF and 52.94 g (499.46 mmol) of anhydrous sodium carbonate, the reaction system was heated to reflux under stirring, the progress of the reaction was monitored by GC, and the disappearance of diethyl malonate was taken as the end of the reaction. After the reaction, the reaction solution was cooled to room temperature and filtered. The filter cake was washed with THF. After the filtrate and the washing solution were combined, the THF was evaporated under normal pressure (recoverable and applied) to obtain crude 1,1-cyclopropyl dicarboxylate 40 g (89% yield). The crude product can be used directly in the next reaction without further purification.

[0045] Into a four-necked flask equipped with a mechanical s...

Embodiment 3

[0046] Example 3: Preparation of 1,1-cyclopropyldimethanol.

[0047] Add 40g (249.73mmol) of diethyl malonate, 37.08g (374.60mmol) of 1,2-dichloroethane, 18.75g (124.87mmol) of sodium iodide, DMA into a four-necked flask equipped with a mechanical stirring device. 300 mL and 62.50 g (624.33 mmol) of anhydrous potassium bicarbonate, the reaction system was heated to reflux under stirring, the progress of the reaction was monitored by GC, and the end of the reaction was the disappearance of diethyl malonate. After the reaction, the reaction solution was cooled to room temperature and filtered. The filter cake was washed with DMA. After the filtrate and washing solution were combined, the DMA was evaporated under normal pressure (recoverable and applied) to obtain crude diethyl 1,1-cyclopropyldicarboxylate 39.5 g (87% yield). The crude product can be used directly in the next reaction without further purification.

[0048] Into a four-necked flask equipped with a mechanical stirring...

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Abstract

The invention belongs to the technical field of drug synthesis and relates to a preparing method for 1,1-cyclopropyl dimethyl carbinol. Specifically, the preparing method for the 1,1-cyclopropyl dimethyl carbinol includes the following steps that firstly, under the participation of a catalyst A, a solvent A and an acid-binding agent, diethyl malonate and 1,2-dichloroethane are used for preparing 1,1-cyclopropyl dioctyl phthalate diethyl ester; and secondly, under the participation of a solvent B and a catalyst B, a reducing agent is used for reducing the 1,1-cyclopropyl dioctyl phthalate diethyl ester, and the target product 1,1-cyclopropyl dimethyl carbinol is obtained. Raw materials adopted in the preparing method are cheap, easy to obtain and free of toxins, the activity of the catalysts are high, the solvents can be recycled, and the cost is obviously reduced; and reaction conditions are moderate, the products are easy to separate, the three industrial wastes are little, and the environment-friendly chemical requirement is met. In addition, according to the preparing method, the yield of the target product can be obviously increased, and the total recovery can reach 88% through the two steps.

Description

Technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to a preparation method of 1,1-cyclopropyldimethanol, a key intermediate for synthesizing montelukast sodium. Background technique [0002] Montelukast sodium (montelukast's sodium carboxylate) is a highly effective, safe, and low-toxic anti-asthmatic, anti-inflammatory and anti-allergic drug. It was developed and produced by Merck in the United States and was first launched in Finland and Mexico in 1998. The drug is a leukotriene receptor antagonist, which can selectively bind with leukotriene receptors in the respiratory tract to block allergic mediators, thereby unblocking the respiratory tract and effectively controlling asthma symptoms. Therefore, these drugs that inhibit the binding of allergens to leukotriene receptors have gradually become the research and development hotspots of anti-asthma drugs. [0003] [0004] 1,1-cyclopropyl dimethanol (also known as 1,1-cyclopropane ...

Claims

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Application Information

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IPC IPC(8): C07C29/147C07C31/27C07C67/343C07C69/74
CPCC07C29/147C07C67/343C07C31/27C07C69/74
Inventor 王凯陈强
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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