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Method for synthesizing (R)-3-amido tetrahydrofuran

A technology of aminotetrahydrofuran and hydroxytetrahydrofuran, which is applied in the field of synthesis of 3-aminotetrahydrofuran, can solve the problems of high toxicity of methyl iodide, large environmental pollution, and difficult availability of raw materials, and achieve the effects of low price, easy availability of raw materials, and reduced production costs

Inactive Publication Date: 2009-01-14
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main limitation of this route is that the raw materials are not easy to get, and more importantly, methyl iodide is used in the process of synthesizing sulfonium iodide
Methyl iodide is highly toxic, pollutes the environment a lot, and is expensive, causing many inconveniences both in production and in use

Method used

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  • Method for synthesizing (R)-3-amido tetrahydrofuran
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  • Method for synthesizing (R)-3-amido tetrahydrofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Step 1. Preparation of (S)-3-tetrahydrofuran p-toluenesulfonate

[0022] (S)-3-Hydroxytetrahydrofuran (3g, 34mmol), p-toluenesulfonyl chloride (9.74g, 51mmol), triethylamine (7ml, 51mmol), DMAP (2.12g, 17mmol) were successively added to 50ml of dichloromethane, stirred, React at 60-70°C for 6-8 hours, TLC detects that the starting material disappears, and the reaction is stopped. Add 150ml of ethyl acetate, and wash with 100ml of 1N dilute hydrochloric acid, 100ml of water, and 100ml of saturated brine. After concentration under reduced pressure, 50 ml of water and 1 g of sodium hydroxide were added and stirred overnight. Extract with ethyl acetate 3 times, 30ml each time, combine the organic phases, and dry over anhydrous magnesium sulfate. Concentration under reduced pressure gave 7.26 g of (S)-3-tetrahydrofuran p-toluenesulfonate as a white solid, with a yield of 88%.

[0023] [ α ] D ...

Embodiment 2

[0033] Step 1. Preparation of (S)-3-tetrahydrofuran mesylate

[0034] (S)-3-Hydroxytetrahydrofuran (3g, 34mmol), methanesulfonyl chloride (5.84g, 51mmol), triethylamine (7ml, 50mmol), DMAP (2g, 16mmol) were added successively to 50ml of dichloromethane, stirred, 50~ React at 60°C for 6-8 hours, and stop the reaction when there is no raw material point detected by TLC. Add 150ml of ethyl acetate, and wash with 100ml of 1N dilute hydrochloric acid, 100ml of water, and 100ml of saturated brine. After concentration under reduced pressure, 50 ml of water and 1 g of sodium hydroxide were added and stirred overnight. Extract with ethyl acetate 3 times, 30ml each time, combine the organic phases, and dry over anhydrous magnesium sulfate. Concentration under reduced pressure gave 4.93 g of light yellow liquid with a yield of 87.1%.

[0035] Step 2. Preparation of (R)-3-aminotetrahydrofuran is the same as in Example 1.

Embodiment 3

[0037] Step 1. Preparation of (S)-3-tetrahydrofuran benzenesulfonate

[0038] (S)-3-Hydroxytetrahydrofuran (3g, 34mmol), benzenesulfonyl chloride (9g, 51mmol), triethylamine (7ml, 50mmol), DMAP (2g, 16mmol) were successively added to 50ml of chloroform, stirred, 60-70 ℃ reaction, 6-8 hours, TLC detection no raw material point, stop the reaction. Add 150ml of ethyl acetate, and wash with 100ml of 1N dilute hydrochloric acid, 100ml of water, and 100ml of saturated brine. After concentration under reduced pressure, 50 ml of water and 1 g of sodium hydroxide were added and stirred overnight. Extract with ethyl acetate 3 times, 30ml each time, combine the organic phases, and dry over anhydrous magnesium sulfate. Concentration under reduced pressure afforded 6.71 g of white solid with a yield of 86.3%.

[0039] Step 2. Preparation of (R)-3-aminotetrahydrofuran is the same as in Example 1.

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Abstract

A process for synthesizing (R)-3-aminotetrahydrofuran includes reaction between (S)-3-hydroxytetrahydrofuran and sulfonyl chloride under existance of 4-dimethylaminopyridine and triethylamine to generate sulfonate, reacting on sodium azide to generate (R)-3-azidotetrahydrofuran, and catalytic hydrogenation reaction.

Description

technical field [0001] The invention relates to a method for synthesizing (R)-3-aminotetrahydrofuran by using (S)-3-hydroxytetrahydrofuran as a raw material. Background technique [0002] (R)-3-Aminotetrahydrofuran 1 is an important intermediate and a key synthetic intermediate for the synthesis of the antiarrhythmic drug Tecadenoson. The structural formula of this compound is shown below. [0003] [0004] (R)-3-aminotetrahydrofuran 1 [0005] The method of the synthetic 3-aminotetrahydrofuran of having reported mainly contains following two kinds: [0006] (1) 3-tetrahydrofuran carboxylic acid reacts with diphenylphosphoryl azide (DPPA) to obtain isocyanate, which then reacts with benzyl alcohol to generate N-benzyloxycarbonyl-3-aminotetrahydrofuran, which is debenzyloxy by catalytic hydrogenation on palladium-carbon Carbonyl protection gives 3-aminotetrahydrofuran (Patent US 5789416), the synthetic route is as follows: [0007] [0008] (2) 4-methylthio 2-triphen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/08
Inventor 靳立人时晓军
Owner XIAMEN UNIV
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