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A kind of synthetic method of 5-hydroxytetrahydrofuran derivative

A synthetic method and generative technology, applied in the direction of sugar derivatives, sugar derivatives, sugar derivatives preparation, etc., can solve the problems of low reaction yield, high price, difficult purification, etc., and achieve high yield and low cost. Low, little environmental pollution effect

Active Publication Date: 2018-02-27
NANJING OCEAN PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The reaction yield of this reduction method is not high, and the product is relatively miscellaneous and difficult to purify.
And LiAlH(t-BuO) 3 The price is also more expensive, there is a certain cost pressure
LiAlH(t-BuO) used in general industry 3 Prepared from lithium tetrahydrogen aluminum, the preparation process is relatively dangerous

Method used

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  • A kind of synthetic method of 5-hydroxytetrahydrofuran derivative
  • A kind of synthetic method of 5-hydroxytetrahydrofuran derivative
  • A kind of synthetic method of 5-hydroxytetrahydrofuran derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 500ml reaction flask, compound I (20g, 53.7mmol) was dissolved in 200mL THF. Under nitrogen protection, the system was cooled to 0°C, and sodium borohydride (0.75g, 19.8mmol) was added to keep the temperature constant during the addition. Over 0°C, after the dropwise addition, stirred for 4h, added sodium borohydride (0.75g, 19.8mmol), and then continued to stir for 4h. Spot the plate to detect the complete reaction of the raw material.

[0027] Add the system to 200ml ice methanol, stir for 30min, recover dry methanol and THF under reduced pressure. Add 200ml of dichloromethane to the residue, stir to dissolve, and control the temperature below 10°C. 250ml of iced ammonium chloride solution was added to the organic phase to wash once, and then washed once with 250ml of saturated brine, and the organic phase was dried and concentrated to obtain 19.7g of compound II with a yield of 98%.

Embodiment 2

[0029] Dissolve compound I (20g, 53.7mmol) in 200mL THF in a 500ml reaction flask, under nitrogen protection, cool the system to 0°C, add sodium acetate borohydride (5.69g, 19.8mmol), keep the temperature during the dropwise addition It does not exceed 0°C. After the dropwise addition, stir for 4h, add sodium acetate borohydride (5.69g, 19.8mmol), and continue stirring for 16h. Spot the plate to detect the complete reaction of the raw material.

[0030] Add the system to 200ml ice methanol, stir for 30min, recover dry methanol and THF under reduced pressure. Add 200ml of dichloromethane to the residue, stir to dissolve, and control the temperature below 10°C. 250ml of iced ammonium chloride solution was added to the organic phase to wash once, and then washed once with 250ml of saturated brine, and the organic phase was dried and concentrated to obtain 19.1g of compound II with a yield of 95%.

Embodiment 3

[0032] Compound I (20g, 53.7mmol) was dissolved in 200mL of toluene in a 500ml reaction flask. Under nitrogen protection, the system was cooled to 0°C, and potassium borohydride (1.07g, 19.8mmol) was added to keep the temperature constant during the addition. Over 0°C, after the dropwise addition, stirred for 4h, added potassium borohydride (1.07g, 19.8mmol), and then continued to stir for 4h. Spot the plate to detect the complete reaction of the raw material.

[0033] Add the system to 200ml ice methanol, stir for 30min, recover dry methanol and toluene under reduced pressure. Add 200ml of dichloromethane to the residue, stir to dissolve, and control the temperature below 10°C. 250ml of iced ammonium chloride solution was added to the organic phase to wash once, and then washed once with 250ml of saturated brine, and the organic phase was dried and concentrated to obtain 19.3g of compound II with a yield of 96%.

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Abstract

The invention discloses a synthetic method for a 5-hydroxytetrahydrofuran derivative, which belongs to the field of organic synthesis. According to the method, a compound shown in a formula I as described in the specification is produced from a compound shown in a formula II as described in the specification through a reduction reaction. According to a technical scheme in the invention, a specific variety and a specific usage amount of a reduction reagent, a specific reaction solvent and specific reaction temperature are selected so as to realize high-selectivity reduction of a carbonyl group into a hydroxy group. The method provided by the invention has the advantages of low cost, mild reaction conditions, few by-products, high yield, small pollution to the environment and capacity of realizing industrial large-scale production.

Description

technical field [0001] The present invention relates to the field of organic synthesis. Specifically, it relates to a synthesis method of 2-benzoic acid methyl group-3-benzoyloxy-4-fluoro-4-methyl-5-hydroxyl-tetrahydrofuran. Background technique [0002] The traditional methods for preparing compound II usually have defects such as high material cost, high reaction conditions, and low conversion rate. [0003] The Chinese name of compound Ⅱ is 2-benzoic acid methyl group-3-benzoyloxy-4-fluoro-4-methyl-5-hydroxy-tetrahydrofuran; the chemical structural formula is: [0004] [0005] In WO 2013 / 178571 A1, WO 2010 / 075549 A2 and other publications, several different synthetic methods for preparing compound II have been reported. [0006] In the WO 2013 / 178571 A1 publication, the synthesis method of Compound II was reported using sodium dihydrobis(2-methoxyethoxy)aluminate (also known as red aluminum) as a reducing agent. The preparation route is as follows: [0007] [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H1/00
CPCC07D307/20
Inventor 陈本顺周长岳邱磊
Owner NANJING OCEAN PHARMA TECH