Synthesis method of 3-hydroxy-1-adamantanecarboxylic acid

A technology of adamantanecarboxylic acid and a synthesis method, applied in the field of organic synthesis, can solve the problems of complexity, expensive raw materials, low yield and the like, and achieve the effects of simple operation, convenient post-processing and high yield

Inactive Publication Date: 2019-05-03
赵明
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 3-Hydroxy-1-adamantanecarboxylic acid is used as a raw material for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid, an important intermediate of saxagliptin. There are many literatures on its synthesis method Covered, but not enough
The current synthetic route is relatively complicated, the price of raw materials is expensive, and the yield is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 0.028 mol of 1-adamantanecarboxylic acid and 0.002 mol of TEBAC into a 150 ml three-necked flask, then add 50 ml of 5% aqueous sodium hydroxide solution and 5 ml of tert-butanol, and stir. The reaction temperature was controlled at 40 °C, then 5.66 g (0.036 mol) of potassium permanganate was added in portions within 0.5 h, and then the temperature was raised to 60 °C and the reaction was stirred for 8.5 h. Add 2.0 g (0.016 mol) of anhydrous sodium sulfite to the reaction vessel to quench the reaction, stir and filter. The black filter cake was washed three times with hot water (15 ml) to obtain a clear filtrate. The clarified filtrate was adjusted to pH 2 with concentrated hydrochloric acid while stirring, and filtered after stirring for 10 min to obtain a white solid. The filtrate was extracted with ethyl acetate (20ml×4 times), the combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was ...

Embodiment 2

[0017] Add 0.030 mol of 1-adamantanecarboxylic acid and 0.002 mol of TEBAC into a 150 ml three-necked flask, then add 50 ml of 5% aqueous sodium hydroxide solution and 5 ml of tert-butanol, and stir. The reaction temperature was controlled at 40 °C, then 5.66 g (0.036 mol) of potassium permanganate was added in portions within 0.5 h, and then the temperature was raised to 60 °C and the reaction was stirred for 8.5 h. Add 2.0 g (0.016 mol) of anhydrous sodium sulfite to the reaction vessel to quench the reaction, stir, and filter. The black filter cake was washed three times with hot water (15 ml) to obtain a clear filtrate. The clarified filtrate was adjusted to pH 2 with concentrated hydrochloric acid while stirring, and filtered after stirring for 10 min to obtain a white solid. The filtrate was extracted with ethyl acetate (20ml×4 times), the combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was...

Embodiment 3

[0018] The influence of embodiment 3 different phase transfer catalysts on reaction yield

[0019] Since 1-adamantanecarboxylic acid has poor water solubility and cannot form a salt with sodium hydroxide in time, in order to shorten the reaction time and improve production efficiency, it is necessary to add a small amount of appropriate co-solvent and phase transfer catalyst to the reaction solution. The applicant chose tert-butanol as a cosolvent and screened three phase transfer catalysts, namely tetrabutylammonium bromide (TBAB), TEBAC, and polyethylene glycol 400 (PEG400). The effects of three phase transfer catalysts with the same phase transfer catalyst-substrate molar ratio (1:14) on the reaction yield and purity were compared by fixing the feeding amount, reaction time, reaction temperature and potassium permanganate-substrate molar ratio . As a result, adding a phase transfer catalyst can increase the reaction yield without affecting the product purity. The catalytic...

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a synthesis method of 3-hydroxy-1-adamantanecarboxylic acid. In the method, with 1-adamantanecarboxylic acid being araw material and triethyl benzyl ammonium chloride (TEBAC) being a phase transfer catalyst, the 3-hydroxy-1-adamantanecarboxylic acid is prepared under alkaline conditions through hydroxylation withKMnO4. The new preparation method not only is reduced in cost and protects environment, but also is simple in operation and convenient in post-treatment. The method is high in yield, is simple in synthesis and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a synthesis method of 3-hydroxy-1-adamantanecarboxylic acid. Background technique [0002] Diabetes is a complex and progressive disease that seriously threatens human health. Its incidence is increasing rapidly all over the world, and it has become the third global disease that endangers human health after tumors and cardiovascular diseases. According to the data updated by the International Diabetes Federation in the 7th edition of "Diabetes Atlas", as of 2015, there were about 415 million diabetic patients in the world. in diabetes. Saxagliptin is the second dipeptidyl peptidase Ⅳ (DPP-Ⅳ) inhibitor antidiabetic drug approved by the US FDA. The drug has obvious hypoglycemic effect, less side effects, good patient compliance and high safety. Advantages, whether it is a single drug or combined with metformin have good therapeutic effects, so it has received...

Claims

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Application Information

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IPC IPC(8): C07C51/367C07C62/06
Inventor 赵明
Owner 赵明
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