A kind of preparation method of 3-aminomethyltetrahydrofuran

A technology for cyanotetrahydrofuran and tetrahydrofuran, applied in directions such as organic chemistry, can solve problems such as difficulty in synthesizing tetrahydrofuran compounds, unfavorable industrial production, expensive ruthenium catalysts, etc., and achieves the effects of low production cost, little environmental pollution, and high utilization rate of raw materials

Active Publication Date: 2018-10-02
北京怡力生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3-Aminomethyltetrahydrofuran is a commonly used intermediate in pharmaceuticals and pesticides. In the prior art, there are few disclosures about its preparation method. The reason is that the substitution reaction of the furan ring can be used to derive tetrahydrofuran compounds with substituents at the 2-position relatively simply. , in contrast, it is very difficult to synthesize tetrahydrofuran compounds with substituents at the 3-position; currently, only the following three methods are disclosed
However, the method has long steps and uses expensive ruthenium catalyst, which is not conducive to industrial production

Method used

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  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: (1) halogenation reaction

[0023]

[0024] Weigh 500g (5.8mol) of γ-butyrolactone into a 1000ml four-necked bottle, equip with condensation and tail gas absorption device, stir and heat to 120°C, start to introduce chlorine gas, the temperature gradually rises to 140°C, and maintain the temperature at 140~ 160°C, continuously feed 494g (6.96mol) of chlorine gas for 12h, then directly rectify the reaction solution under reduced pressure to recover unreacted γ-butyrolactone, and then collect 3-chloro-γ-butyrolactone stably, as Colorless oil, namely 3-chloro-γ-butyrolactone; purity 95%, yield 70%.

[0025]

[0026] (2) Reduction reaction

[0027] Weigh 120g (1.0mol) of 3-chloro-γ-butyrolactone and place it in a 1000ml four-necked bottle, add 500ml of anhydrous methanol to dissolve, add 22.68g (0.6mol) of sodium borohydride in batches at 25°C, and Stir the reaction at 25°C for 4-6 hours, gas phase detection until the reaction is complete, evaporate th...

Embodiment 2

[0041] (1) Halogenation reaction

[0042]Weigh 500g (5.8mol) of γ-butyrolactone into a 1000ml four-necked bottle, equip with condensation and tail gas absorption device, stir and heat to 120°C, start to introduce chlorine gas, the temperature gradually rises to 140°C, and maintain the temperature at 140~ 160°C, continuously feed 494g (6.96mol) of chlorine gas for 12h, then directly rectify the reaction solution under reduced pressure to recover unreacted γ-butyrolactone, and then collect 3-chloro-γ-butyrolactone stably, as Colorless oil, namely 3-chloro-γ-butyrolactone; purity 95%, yield 70%.

[0043] (2) Reduction reaction

[0044] Weigh 120g (1.0mol) of 3-chloro-γ-butyrolactone into a 1000ml four-necked bottle, add 500ml of anhydrous tetrahydrofuran to dissolve, add 37.95g (1.0mol) of lithium tetrahydrohydride in batches at 20°C, and Stir the reaction at 20°C for 3h, the gas phase detects that the reaction is complete, cool down to 0°C, and slowly add 200ml of water under ...

Embodiment 3

[0054] (1) Halogenation reaction

[0055] Weigh 500g (5.8mol) of γ-butyrolactone into a 1000ml four-necked bottle, equip with condensation and tail gas absorption device, stir and heat to 120°C, start to introduce chlorine gas, the temperature gradually rises to 140°C, and maintain the temperature at 140~ 160°C, continuously feed 494g (6.96mol) of chlorine gas for 12h, then directly rectify the reaction solution under reduced pressure to recover unreacted γ-butyrolactone, and then collect 3-chloro-γ-butyrolactone stably, as Colorless oil, namely 3-chloro-γ-butyrolactone; purity 95%, yield 70%.

[0056] (2) Reduction reaction

[0057] Weigh 120g (1.0mol) of 3-chloro-γ-butyrolactone and place it in a 1000ml four-necked bottle, add 500ml of anhydrous methanol to dissolve, add 22.68g (0.6mol) of sodium borohydride in batches at 25°C, and Stir the reaction at 25°C for 6 hours. When the gas phase detects that the reaction is complete, distill methanol off under reduced pressure, a...

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Abstract

The invention relates to a preparation method of 3-aminomethyl tetrahydrofuran. Specifically the invention relates to a method of preparing 3-aminomethyl tetrahydrofuran through reducing 3-cyanotetrahydrofuran. A novel synthesis technology is adopted; gamma-butyrolactone and a halogen simple substance X2 are taken as the raw materials to prepare 3-X-gamma-butyrolactone; then 3-X-gamma-butyrolactone is reduced by a reducing agent to obtain 2-X-1,4-butylene glycol; 2-X-1,4-butylene glycol is dehydrated by a dehydrating agent to obtain 3-X tetrahydrofuran; 3-X tetrahydrofuran is converted into 3-cyanotetrahydrofuran in the presence of a cyaniding catalyst, and finally 3-cyanotetrahydrofuran is converted into 3-aminomethyl tetrahydrofuran in the presence of a hydrogenation catalyst. The synthesis technology has the advantages of easily available raw materials, simple operation, mild reaction conditions, high yield and product purity, little environmental pollution, and low production cost, is suitable for industrial massive production, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a preparation method of 3-aminomethyltetrahydrofuran, in particular to a method for preparing 3-aminomethyltetrahydrofuran by a reduction method. Background technique [0002] 3-Aminomethyltetrahydrofuran is a commonly used intermediate in pharmaceuticals and pesticides. In the prior art, there are few disclosures about its preparation method. The reason is that the substitution reaction of the furan ring can be used to derive tetrahydrofuran compounds with substituents at the 2-position relatively simply. , in contrast, it is very difficult to synthesize a tetrahydrofuran compound having a substituent at the 3-position; currently, only the following three methods are disclosed. [0003] (1) As one of the preparation methods of 3-aminomethyltetrahydrofuran, it is known to use tetrahydrofuran-3-carbaldehyde as a raw material for reductive amination in the presence of hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 张立刚李梦菲王瑞邓旭芳陈建伟王文军
Owner 北京怡力生物科技有限公司
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