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Method for synthesizing 3,5-dibasic-1-adamantine alcohol

A technology of adamantanol and a synthetic method, applied in 3 fields, can solve the problems such as high price of DDQ oxidant, unsatisfactory purification and yield, and yield of only 86%, and achieves low cost, short reaction time, and solvent saving. Effect

Inactive Publication Date: 2005-08-31
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

[0003] Regarding the synthesis of adamantanol compounds, literature reports mainly adopt oxidation methods such as ozone, hydrogen peroxide, and peroxide, but the products obtained by oxidation of adamantane by these oxidants often contain 2-alcohol, 2-alcohol, The presence of ketones and 1,3-diols, the purification and yield are not ideal
Document J Chem Soc Perkin Trans I (2001, P3230-3231) reported that DDQ was used as an oxidant, and in CF 3 A single 1-alcohol is obtained by reacting in COOH solution, but on the one hand, the price of DDQ oxidant is relatively expensive, and at the same time, the method uses column chromatography to separate and purify the product, the cost is high, and the yield is only 86%.

Method used

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  • Method for synthesizing 3,5-dibasic-1-adamantine alcohol
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  • Method for synthesizing 3,5-dibasic-1-adamantine alcohol

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Embodiment 1

[0019] Weigh 6.20g (0.0455mol) of adamantane into a 250ml three-neck round bottom flask, stir, add 18ml (0.351mol) of bromine dropwise, and react at 60°C for 2 hours; add 25.0g (0.187mol) to the above reaction solution Sodium oxalate and 55ml of water were reacted at 75°C for 40 minutes, cooled, filtered with suction, and washed with water to obtain 6.86g of 1-adamantanol, yield: 99.05%. mp: 278~280℃; MS: m / z: 152(M + ), 95; 1 H NMR (400Hz, CDCl 3 )2.137 (3H, -CH), 1.60-1.715 (10H, -CH 2 ), 1.70 (1H, -OH); IR (KBr): 3283, 2954, 2851, 1454, 1353, 1118, 1089.

Embodiment 2

[0021] Weigh 6.20g (0.0455mol) of adamantane into a 250ml three-neck round bottom flask, stir, add 12ml (0.234mol) of bromine dropwise, and react at 35°C for 3 hours; add 13.3g (0.099mol) to the above reaction solution Sodium oxalate and 70ml of water were reacted at 55°C for 110 minutes, cooled, suction filtered and washed with water to obtain 6.65g of 1-adamantanol, yield: 96.02%.

Embodiment 3

[0023] Weigh 6.20g (0.0455mol) of adamantane into a 250ml three-neck round bottom flask, stir, add 24ml (0.468mol) of bromine, and react at 70°C for 1 hour; add 36.6g (0.273mol) of oxalic acid to the above reaction solution Sodium and 80ml of water were reacted at 80°C for 25 minutes, cooled, filtered with suction, and washed with water to obtain 6.88g of 1-adamantanol, yield: 99.35%.

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Abstract

A process for synthesizing 3,5-disubstituent-1-adamantanol includes reaction between 1,3-disubstituent adamantane and bromine to obtain bromo compound, adding sodium oxalate and water, reaction, filtering and washing.

Description

technical field [0001] The invention relates to a synthesis method of 3,5-disubstituted-1-adamantanol. Background technique [0002] Adamantane is a caged saturated hydrocarbon. Its unique physical and chemical properties are determined by its rigid system and high symmetry structure. Adamantane and its derivatives are widely used in many fields such as medicine, functional polymers, lubricants, catalysts, surfactants, photosensitive materials, and pesticides. This type of compound was mainly used for anti-influenza A virus in the early stage. With the deepening of research, it was found that adamantane derivatives, especially their amine derivatives, have various biological activities. Such as amantadine not only has anti-influenza virus effect, but also has anti-HSV virus and antifungal effect; another example is the dementia treatment drug memantine developed by German Merz Company, which is used for the treatment of moderate to severe dementia and has achieved good re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/09C07C35/37
Inventor 邹永杨国立张学景何树杰魏文
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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