Method for efficiently synthesizing beta-benzyl butyrolactone having specific configuration

A technology of benzylbutyrolactone and configuration, applied in the field of medicine, can solve the problems of poor substrate applicability, difficult preparation of raw materials, and high preparation cost, and achieve the effects of short steps, cheap raw materials and high optical purity

Active Publication Date: 2015-12-23
LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Abstract
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Problems solved by technology

[0006] 2. This method is only applicable to the preparation of β-benzylbutyrolactone in R configuration;
[0007] 3. The total yield is low, only 7.4-34.7%, especially in the NMO oxidation step, the yield is only about 50%
[0008] 4. Since the hydrogenation reaction requires the use of specific equipment, the overall preparation cost is too high
[0015] The raw materials are not easy to prepare, the substrate applicability is not strong, and the optical purity is low

Method used

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  • Method for efficiently synthesizing beta-benzyl butyrolactone having specific configuration
  • Method for efficiently synthesizing beta-benzyl butyrolactone having specific configuration
  • Method for efficiently synthesizing beta-benzyl butyrolactone having specific configuration

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Embodiment

[0042] 1. Preparation of (R)-β-(3,4-dimethoxybenzyl)butyrolactone

[0043]

[0044] 3,4-dimethoxyphenylpropionic acid (2.1g, 10mmol, 1.0eq.) was dissolved in 60mL of anhydrous THF, pivaloyl chloride (1.2mL, 10mmol, 1.0eq.) was added dropwise at -20°C and Triethylamine (4.2mL, 30mmol, 3.0eq.), continue stirring for 20min. A THF solution (20 mL) of (S)-4-benzyl-2-oxazolidinone (1a, 1.6 g, 9.0 mmol, 0.9 eq.) was added dropwise, and LiCl (420 mg, 10 mmol, 1.0 eq.) was added in one portion , Stirring was continued at this temperature for 20 min. Then it was raised to room temperature and stirred for 2h. TLC showed the starting material was completely reacted. The reaction solution was concentrated under reduced pressure to about 20 mL, diluted with ethyl acetate, washed successively with 5% aqueous potassium bisulfate solution, 10% aqueous sodium bicarbonate solution, and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate w...

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Abstract

The present invention discloses a method for efficiently synthesizing beta-benzyl butyrolactone having a specific configuration. The method is characterized in that phenylpropionic acid or a derivative thereof is adopted as a starting material, the phenylpropionic acid or the derivative thereof and an oxazolidone chiral prosthetic group are subjected to condensation, a haloacetic acid ester attacks the carbonyl ortho position carbon of the phenylpropionic acid under the effect of a large steric hindrance organic alkali, the prosthetic group is hydrolyzed and recovered after the specific chiral center is successfully constructed, and the corresponding product is subjected to an intramolecular ester exchange reaction to generate the beta-benzyl butyrolactone having the specific configuration. According to the present invention, the prepared beta-benzyl butyrolactone can be used for chemical synthesis of a lot of dibenzyl type lignins having potential medicinal values, and has characteristics of cheap and readily available raw materials, short step, high yield, and high optical purity.

Description

Technical field: [0001] The invention relates to a preparation method of an important pharmaceutical intermediate, in particular to a method for efficiently synthesizing β-benzylbutyrolactone with a specific configuration, which belongs to the field of medicine. technical background: [0002] According to literature reports (Kamlage, S.et.al.Chem.Comm.), β-benzylbutyrolactone can be prepared by the following route: [0003] [0004] This method has following deficiencies: [0005] 1. This method requires a total of 4 steps of reaction, and each step requires the use of catalysts, and 3 of them require the use of precious metal catalysts; [0006] 2. This method is only applicable to the preparation of β-benzylbutyrolactone in R configuration; [0007] 3. The total yield is low, only 7.4-34.7%, especially in the NMO oxidation step, the yield is only about 50%. [0008] 4. Since the hydrogenation reaction needs to use specific equipment, the overall preparation cost is t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 翟延君吴平康廷国初正云
Owner LIAONING UNIV OF TRADITIONAL CHINESE MEDICINE
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