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Method for preparing tetrahydrofuran-3-boric acid pinacol ester

A technology of tetrahydrofuran and dihydrofuran, which is applied in the field of organic chemical synthesis, can solve the problems of expensive raw material pinacol borane and transition metal catalyst, restrict mass production of target products, and cannot realize enlarged production, etc. The effect of high yield and low product cost

Inactive Publication Date: 2015-06-03
成都安斯利生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, not only the raw material pinacol borane and the transition metal catalyst are expensive and difficult to obtain, but also the reaction generates two positional isomer products, which are difficult to separate and purify, the reaction efficiency is low, the raw material utilization rate is low, and the reaction conditions are harsh. , can only be synthesized at the mil

Method used

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  • Method for preparing tetrahydrofuran-3-boric acid pinacol ester
  • Method for preparing tetrahydrofuran-3-boric acid pinacol ester
  • Method for preparing tetrahydrofuran-3-boric acid pinacol ester

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Experimental program
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Effect test

Embodiment 1

[0027] In a 1L three-necked reaction flask, add D-α-pinene (50g, 0.37mol) and 200mL of anhydrous tetrahydrofuran. 0.17mol, 10M in dimethylsulfide), after the addition, the temperature was raised to room temperature, reacted for 4h, and a white solid was generated, then the reaction solution was cooled to -40°C, and 2,5-dihydrofuran (12g, 0.17mol ), after the addition was completed, after rising to room temperature, reacted for 12h, added anhydrous acetaldehyde (75g, 1.7mol), reacted at room temperature for 6h, removed excess anhydrous acetaldehyde under reduced pressure, and then pinacol (20.1g, 0.17 mol), reacted at room temperature for 12h, and evaporated the solvent under reduced pressure with a rotary evaporator, and collected 107-109°C / 1mmHg fractions by distillation under reduced pressure to obtain 24.2g of a colorless liquid, which was tetrahydrofuran-3-boronic acid pinacol ester. rate of 72%. 1H NMR (CD 3 Cl): 3.99ppm, multimodal (1H); 3.80ppm, multimodal (1H); 3.70p...

Embodiment 2

[0029] In a 10L three-necked reaction flask, add D-α-pinene (2331.15g, 17.11mol) and 2.5L anhydrous tetrahydrofuran, under the protection of nitrogen, cool to 0 ° C, slowly dropwise add borane dimethyl sulfide complex ( 815mL, 8.15mol, 10M in dimethylsulfide), after the addition, the temperature was raised to room temperature, and reacted for 4h to generate a white solid, then the reaction solution was cooled to -40°C, and 2,5-dihydrofuran (571g, 8.15mol), the addition was completed, after rising to room temperature, reacted for 12h, added anhydrous acetaldehyde (3690g, 81.5mol), reacted at room temperature for 6h, removed excess anhydrous acetaldehyde under reduced pressure, and then pinacol (963g, 8.15mol), reacted at room temperature for 12h, evaporated the solvent under reduced pressure with a rotary evaporator, collected 107-109°C / 1mmHg fraction by distillation under reduced pressure, and obtained 1097.3g of a colorless liquid, which was tetrahydrofuran-3-boronic acid pina...

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Abstract

The invention discloses a method for preparing tetrahydrofuran-3-boric acid pinacol ester. The method comprises the following steps: preparing bi-alpha-isopoinocamphenylborane by using dextro-alpha-pinene and borane-methyl sulfide complex as raw materials; then performing reaction on bi-alpha-isopoinocamphenylborane and 2,5-dihydrofuran at a room temperature; performing reduction by using anhydrous acetaldehyde to produce bimethyl borate without needing separation of a midbody; subsequently, performing reaction on bimethyl borate and pinacol to produce a tetrahydrofuran-3-boric acid pinacol ester target product. The method has the obvious advantages of easily-available reaction raw materials, simple reaction operation, easiness for realization of large-scale production, high yield, high purity and low production cost.

Description

technical field [0001] The invention relates to a new method for synthesizing a pharmaceutical intermediate organic borate, belonging to the field of organic chemical synthesis, in particular to a method for preparing tetrahydrofuran-3-boronic acid pinacol ester. Background technique [0002] Organoboronic acid and its derivatives are an important class of pharmaceutical intermediates and organic chemical reagents, which are widely used in organic synthesis to form new C-C single bonds through Suzuki-Miyaura coupling reactions. Most organic boronic acids are stable at room temperature and can be stored for a long time, but some alkyl boronic acids and alkene or alkyne boronic acids are unstable at room temperature and are prone to deterioration, so it is difficult to preserve this type of boronic acid. Certain difficulties, if this type of boric acid is converted into boric acid derivatives such as boric acid esters, its properties are stable and can be stored for a period o...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/04
Inventor 唐拥军莫珊刘玉琴
Owner 成都安斯利生物医药有限公司
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