3-amino-1-adamantanol and synthesis method thereof

A technology for adamantanol and a synthesis method, which is applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of difficult industrialization of reaction conditions, low total yield, and many steps, and achieves reduced The effect of high production cost, high yield and high efficiency

Pending Publication Date: 2021-04-23
广东仁康达材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The preparation method of 3-amino-1-adamantanol has following several at present: (1) take amantadine hydrochloride as raw material, by H 2 SO 4 / HNO 3 System oxidation, then alkaline hydrolysis, solvent extraction and other post-treatments to obtain 3-aminoadamantanol; the raw materials of this method are uneconomical
(2) Using adamantanecarboxylic acid as a raw material, the target product is synthesized in four steps such as bromination, azidation, Curtis rearrangement, and hydrolysis. This synthetic method has many steps, the total yield is not high, and requires Using diphenylphosphoryl azide has higher cost and is not suitable for industrial production
(3) take amantadine as raw material, molybdenum hexacarbonyl is a catalyzer, and carbon tetrabromide is an oxidant to prepare 3-aminoadamantanol, and the yield is 80%; the used catalyzer of this method is expensive, and the cost is very high
(4) take amantadine hydrochloride as raw material, carry out selective oxidation with trifluoroacetone as oxidant to obtain the target product; the used trifluoroacetone of this method is unstable and difficult to obtain, and the reaction conditions are difficult to industrialize

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  • 3-amino-1-adamantanol and synthesis method thereof
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  • 3-amino-1-adamantanol and synthesis method thereof

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preparation example Construction

[0030] In one embodiment, the preparation method of 3-acetamido-1-adamantanol comprises: mixing adamantane and strong acid, stirring at 30-100°C for 0.5-3h, and stirring at 30°C within 20-60min Complete the dropwise addition of the nitrile compound, continue the reaction at 40-60°C for 1-10 hours to obtain the reaction liquid, drop the reaction liquid into the mixed extract for extraction, separate the liquid under the condition that the temperature does not exceed 10°C, and use the extract for the aqueous phase -1 and then extract; combine the organic phases, distill, and obtain.

[0031] Preferably, the nitrile compound is fatty nitrile; further preferably, the fatty nitrile is acetonitrile and / or propionitrile; more preferably, the fatty nitrile is acetonitrile.

[0032] In a preferred embodiment, the preparation method of 3-acetamido-1-adamantanol comprises: mixing adamantane and a strong acid, stirring at 30°C for 0.5h, and completing the dropwise addition within 60min be...

Embodiment 1

[0051] Embodiment 1 of the present invention provides a kind of synthetic method of 3-amino-1-adamantanol, and its concrete steps are: (1) adamantane and strong acid are mixed, stirred at 30 ℃ for 3h, under 30 ℃ in 60min The nitrile compound was added dropwise, and the reaction solution was obtained after continuing the reaction at 40°C for 10 hours. The reaction solution was dropped into the mixed extraction liquid for extraction, and the liquid was separated under the condition that the temperature did not exceed 10°C. Perform extraction; combine the organic phases and distill to obtain 3-acetamido-1-adamantanol; (2) mix 3-acetamido-1-adamantanol, strong base, and alcohol solvent, heat up to 160°C in airtight conditions, After reacting for 10 hours, cool and crystallize, filter, wash the filter cake with an alcohol solvent, combine the filtrates, and distill off the solvent to obtain the product.

[0052] The weight ratio of the 3-acetylamino-1-adamantanol, strong base, and ...

Embodiment 2

[0054] Embodiment 2 of the present invention provides a synthetic method of 3-amino-1-adamantanol, the specific steps of which are: (1) mix adamantane with a strong acid, stir at 30°C for 0.5h, and place under 30°C in Complete the dropwise addition of the nitrile compound within 60 minutes, continue the reaction at 60°C for 1 hour to obtain the reaction liquid, drop the reaction liquid into the mixed extract for extraction, separate the liquid under the condition that the temperature does not exceed 10°C, and use the extract-1 for the aqueous phase Then extract; combine the organic phases and distill to obtain 3-acetamido-1-adamantanol; (2) mix 3-acetamido-1-adamantanol, strong base, and alcohol solvent, and heat up to 200°C , After reacting for 5h, cool and crystallize, filter, wash the filter cake with an alcohol solvent, combine the filtrates, and distill off the solvent to obtain that product.

[0055] The weight ratio of the 3-acetylamino-1-adamantanol, strong base, and a...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to 3-amino-1-adamantanol and a synthesis method thereof. The synthesis method of 3-amino-1-adamantanol comprises the following steps of: mixing 3-acetyl amino-1-adamantanol, strong base and an alcohol solvent, heating to 100-200 DEG C in a closed environment, reacting for 5-10h, cooling, crystallizing, filtering, washing the filter cake with the alcohol solvent, merging the filtrate, and distilling to remove the solvent, thereby obtaining the 3-amino-1-adamantanol. The synthesis method of 3-amino-1-adamantanol provided by the invention has the characteristics of simple steps, easiness in operation, high yield, high efficiency and suitability for industrial production; and the used raw material is adamantane, and special adamantane derivatives such as amantadine and adamantanecarboxylic acid are not needed as raw materials, so that the production cost is further reduced.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, more specifically, the present invention relates to a kind of 3-amino-1-adamantanol and its synthesis method. Background technique [0002] The incidence of diabetes is increasing year by year, and it has become one of the three major chronic diseases that threaten human health. Traditional oral drugs for treating diabetes mainly include: sulfonylureas, biguanides, glinides, thiazolidinediones, α-glucosidase inhibitors, etc. The dipeptidyl peptidase-IV (DPP-IV) inhibitors that have been on the market in recent years are widely used because of their definite hypoglycemic effect, low risk of hypoglycemia, and non-obesity-induced effects. [0003] Vildagliptin is a highly selective dipeptidyl peptidase inhibitor developed by Novartis. It was approved for marketing by the European Union in 2008 and entered the Chinese market in 2011. Its global sales in 2019 are close to 13 One hu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C215/44C07C231/06C07C231/24C07C233/23
CPCC07C213/02C07C215/44C07C231/06C07C231/24C07C2603/74C07C233/23
Inventor 黄志健卢立鹏梁学文庞海舰
Owner 广东仁康达材料科技有限公司
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