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Novel method for preparing S-3-hydroxytetrahydrofuran

A technology of hydroxytetrahydrofuran and S-3-, which is applied in the direction of organic chemistry, can solve the problems of using too much solvent, unfavorable industrial production, and low yield, and achieves the effects of low cost, favorable product separation, and low pollution

Inactive Publication Date: 2012-05-30
苏州凯达生物医药技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 2. Using S-4-chloro-3-hydroxybutyric acid ethyl ester as raw material, after reduction, dehydrochlorination and cyclization under acidic conditions to obtain the target product [US 6359155; Applied Chemical Industry 2008, 37: 191-193]; in the current S Under the premise that ethyl 4-chloro-3-hydroxybutyrate has been industrialized, this method has the advantages of short synthetic route and easy operation; but the intermediate product and final product are very water-soluble, and the product is difficult to obtain from the aqueous phase system. Extraction will lead to the disadvantages of using a large amount of solvent and low yield, which is not conducive to the realization of industrial production

Method used

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  • Novel method for preparing S-3-hydroxytetrahydrofuran
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  • Novel method for preparing S-3-hydroxytetrahydrofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Step 1, the preparation of S-4-chloro-3-methoxybutyric acid ethyl ester.

[0033] Dissolve 100 grams of S-4-chloro-3-hydroxybutyric acid ethyl ester in 500 milliliters of toluene, cool with ice water, add 190 grams of sodium carbonate, and slowly add 91 grams of dimethyl sulfate dropwise under vigorous stirring; the addition is complete , gradually rise to room temperature, after GC detects that the reaction of the raw materials is completed, the solid is removed by filtration, the organic layer is washed with saline, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure to obtain 93.4 grams of S-4-chloro-3-methoxybutyl Acetate ethyl ester, yield 86%.

[0034] Step 2, the preparation of S-4-chloro-3-methoxy-1-butanol.

[0035] Dissolve 90 grams of S-4-chloro-3-methoxy ethyl butyrate in 150 milliliters of ethanol, cool with ice water, add 23 grams of sodium borohydride, and slowly add 66 grams of calcium chloride dropwise under vigoro...

Embodiment 2

[0042] Step 1: Preparation of ethyl S-4-chloro-3-tert-butoxybutyrate:

[0043] Dissolve 100 g of ethyl S-4-chloro-3-hydroxybutyrate in 400 ml of dichloromethane, add 2 ml of concentrated sulfuric acid, cool to -20°C, and slowly add isobutene until the volume doubles under vigorous stirring ; Gradually rise to room temperature, after GC detects that the raw material has reacted, after washing with ice water, washing with sodium carbonate solution, the organic layer is dried with anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure to obtain 131 grams of S-4-chloro-3-tert-butyl Ethyl oxybutyrate, yield 98%.

[0044] Step 2: Preparation of S-4-chloro-3-tert-butoxy-1-butanol:

[0045] Suspend 18.8 grams of sodium borohydride in 200 milliliters of tetrahydrofuran, control the temperature at 40°C, slowly add 100 grams of tetrahydrofuran solution of S-4-chloro-3-tert-butoxybutyric acid ethyl ester dropwise, dropwise, at 40°C The reaction was complete (GC d...

Embodiment 3

[0053] Step 1: Preparation of ethyl S-4-chloro-3-benzyloxybutyrate

[0054] Dissolve 100 grams of S-4-chloro-3-hydroxybutyric acid ethyl ester in 500 milliliters of tetrahydrofuran, cool with ice water, add 127 grams of sodium carbonate, and slowly add 83.6 grams of benzyl chloride dropwise under vigorous stirring; Gradually rise to room temperature, after the disappearance of raw materials detected by GC, remove the solid by filtration, wash the organic layer with brine, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure to obtain 120 g of S-4-chloro-3-benzyloxybutanoic acid Ethyl ester, yield 78%.

[0055] Step 2: Preparation of S-4-chloro-3-benzyloxy-1-butanol

[0056] Under nitrogen protection, suspend 19 grams of sodium borohydride and 21 grams of lithium chloride in 100 milliliters of tetrahydrofuran, stir vigorously for ten minutes, dissolve 128 grams of S-4-chloro-3-benzyloxy ethyl butyrate in 500 milliliters of ethanol The solution was s...

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Abstract

The invention discloses a novel method for preparing an important medical farm chemical intermediate, i.e., S-3-hydroxytetrahydrofuran. The method comprises the following steps of: performing hydroxy group protection on S-4-chloro-3-hydroxybutyrate serving as a raw material; and undergoing a reduction reaction, a cyclization reaction and a deprotection reaction to obtain a target product. A synthesis method disclosed by the invention has the advantages of high optical purity and high yield of the target product, easiness and convenience for reaction operation, environmentally-friendly process and suitability for industrial production.

Description

technical field [0001] The invention relates to the preparation of medicines, in particular to a new preparation method of S-3-hydroxytetrahydrofuran, an important optically active intermediate of medicine and pesticide. Background technique [0002] Chirality is a common feature in the universe. The nucleotides, amino acids and monosaccharides that constitute the basic substances of life all have chiral characteristics, and the biological macromolecules nucleic acids, proteins and sugars composed of them all have characteristic spatial structures. This configuration characteristic lays the foundation for the generation and evolution of life, and also determines that chiral substances (optical active substances) play an important role in many fields such as medical science, pesticide science, and material science. At present, optically active medicines and pesticides have become a major trend in the development of the pharmaceutical industry and the pesticide industry due to...

Claims

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Application Information

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IPC IPC(8): C07D307/20
Inventor 陆军顾铭肖本良张燕飞杨进
Owner 苏州凯达生物医药技术有限公司
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