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Method for preparing key intermediate 3-amino-1-adamantanol of vildagliptin

A technology for amantadine alcohol and amantadine hydrochloride, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of difficult industrialization, many steps, and high costs, and achieves cost reduction and steps. Simple, easy-to-use ingredients

Active Publication Date: 2014-05-21
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are two synthetic methods of 3-amino-1-adamantanol reported in the literature: one is to synthesize by removing an amino group and hydrolyzing 1,3-adamantanediamine under specific conditions. This method has many steps , reaction selectivity and yield are all low, and cost is high; Another kind is to adopt trifluoroperoxide acetone to carry out selective oxidation to amantadine, and the raw material trifluoroperoxide acetone of this method is difficult to obtain and unstable, industrialization High difficulty

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Add 42ml of trifluoroacetic acid and 200ml of fuming sulfuric acid into a three-necked flask equipped with a thermometer and an exhaust gas absorption device, slowly add 14ml of 65% concentrated nitric acid dropwise under ice bath cooling and stirring, stir for 20-30min, and wait for When the temperature drops to 0°C, add 19 g of amantadine hydrochloride in 6 times within 30 minutes, remove the ice bath after stirring for 2 hours, control the temperature at 20°C, stir for 10 hours, add ice cubes to the reaction solution one by one until When it is clear dark green, move the reaction solution to an ice bath and stir for 30 minutes. After the reaction solution turns white, remove the ice bath, add 89% potassium hydroxide in batches to neutralize it under stirring, and continue stirring until the solution is alkaline. , yielding a white thick solid;

[0017] (2) Suction filter the white thick solid obtained in the previous step, dissolve the obtained solid with dichlor...

Embodiment 2

[0019] (1) Add 85ml of trifluoroacetic acid and 400ml of fuming sulfuric acid into a 1000ml three-necked bottle with a thermometer, slowly add 28ml of 65% concentrated nitric acid dropwise under ice bath cooling and stirring, stir for 20min, and wait until the temperature drops to 0°C Add 40g of amantadine hydrochloride in 8 times within 30 minutes, remove the ice bath after stirring for 3 hours, control the temperature at 20°C, stir for 10 hours, add ice cubes to the reaction solution one by one until the reaction solution is clear and dark green , move the reaction solution to the ice bath and stir for 30 minutes, remove the ice bath, add 89% potassium hydroxide in batches for neutralization under stirring, and continue stirring until the pH of the solution is 14 to produce a white thick solid; (2) The white thick solid obtained in one step was suction filtered, the obtained solid was washed with dichloromethane, extracted, the filtrates were combined, dried over anhydrous ma...

Embodiment 3

[0021] (1) Add 170 ml of trifluoroacetic acid and 800 ml of fuming sulfuric acid into a three-necked flask equipped with a thermometer and an exhaust gas absorption device, slowly add 56 ml of 65% concentrated nitric acid dropwise under ice cooling and stirring, and stir for 30 minutes. When the temperature drops to 0°C, add 76g of amantadine hydrochloride in 8 times within 30 minutes, remove the ice bath after stirring for 3 hours, control the temperature at 20°C, stir for 10 hours, add ice cubes to the reaction solution one by one until the reaction When the solution is clear, move the reaction solution to an ice bath and stir for 30 minutes. After the reaction solution turns white, remove the ice bath, add 89% potassium hydroxide in batches for neutralization under stirring, and continue stirring until the solution is strongly alkaline. , yielding a white thick solid;

[0022] (2) Suction filter the white thick solid obtained in the previous step, wash the obtained solid wi...

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Abstract

The invention relates to a method for preparing key intermediate 3-amino-1-adamantanol of vildagliptin. The 3-amino-1-adamantanol is prepared by taking low-price amantadine hydrochloride as an initial raw material and adopting a mixed acid method in which different acids are changed. The method is mainly characterized in that the rate of charge of fuming sulphuric acid, trifluoroacetic acid, nitric acid and amantadine hydrochloride in reaction and temperature and time in the reaction process are controlled, so that the yield of the product is greatly improved. In addition, the method provided by the invention further has the advantages of available raw material, low price, mild reaction condition, short time, less environmental pollution, cost reduction due to recycled solvent and the like, and is simple to operate and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical engineering and relates to a preparation method of 3-amino-1-adamantanol, a key intermediate of vildagliptin. Background technique [0002] Diabetes mellitus is a group of metabolic diseases characterized by hyperglycemia caused by defective insulin secretion or its biological action, or both. Diabetes is long-standing hyperglycemia, which leads to chronic damage and dysfunction of various tissues, especially the eyes, kidneys, heart, blood vessels, and nerves. It is a chronic disease that plagues the world. There are currently about 230 million patients worldwide, and it is estimated that the number of patients will increase to 350 million by 2025. Diabetes is the fourth leading cause of death in most countries, and if left untreated or undertreated, type 2 diabetes can lead to heart and kidney disease, blindness, and vascular and neuropathy. On September 28, 2007, Novartis announced tha...

Claims

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Application Information

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IPC IPC(8): C07C215/44C07C213/00
Inventor 张梅彭学东赵金召叶俊
Owner ZHANG JIA GANG VINSCE BIO PHARM
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