4-(aminomethyl)chromane-3-ol preparation method

A technology of aminomethyl and chromane, which is applied in the field of synthesis of 4-chroman-3-ol, can solve the problems of no suitable industrial synthesis method, and achieve the effects of convenient operation, easy reaction and short route

Active Publication Date: 2019-12-13
上海合全医药有限公司
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Mainly solve the technical problem that there is

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Embodiment 1

[0011] Example 1: a. Compound 1 (20.00 g, 161.11 mmol) and sodium cyanide (8.69 g, 177.22 mmol) were miscible in a nitrogen nitrogen dimethylformamide solution (200.00 mL). Control the temperature at 120°C and stir for 4 hours. TLC (volume ratio of petroleum ether / ethyl acetate = 2 / 1) indicated the end of the reaction. The reaction solution was poured into water (600 mL), and then the aqueous phase was extracted with ethyl acetate (100 mL * 6). The organic phases were combined, dried with sodium sulfate, filtered and concentrated by distillation under reduced pressure to obtain a crude product. The crude product was purified on a silica gel column (dichloromethane / methanol volume ratio = 10 / 1) to obtain compound 2 (3.5 g) as a yellow oil with a yield of 16.32%.

[0012] b. Dissolve compound 2 (1.50 g, 11.27 mmol) and ethyl bromoacetate (1.88 g, 11.27 mmol) in acetone (30.00 mL), then add potassium carbonate (4.67 g, 33.80 mmol) in batches, and the reaction solution Slowly rise...

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Abstract

The invention relates to a 4-(aminomethyl)chromane-3-ol preparation method. A purpose of the present invention is mainly to solve the technical problem that no suitable industrial synthesis method exists in the prior art. According to the present invention, the method comprises four steps, and comprises: generating a compound 2 from a compound 1 and a compound sodium cyanide in a solvent N,N-dimethylformamide, carrying out a reaction on the compound 2 and ethyl bromoacetate in acetone to obtain a compound 3, carrying out a reaction on the compound 3 and sodium in acetone to obtain a compound 4, and carrying out a reaction on the compound 4, ammonia water and Raney nickel in acetone under the condition of hydrogen introducing to obtain a final compound 5. According to the present invention,the obtained compound can be used as the intermediate or product for synthesis of a plurality of drugs.

Description

Technical field [0001] The present invention relates to a synthesis method of 4-(aminomethyl)chroman-3-ol (MFCD28636717). Background technique [0002] 4-(Aminomethyl)chroman-3-ol and related derivatives have a wide range of applications in medicinal chemistry and organic synthesis. At present, there is little synthesis of 4-(aminomethyl)chroman-3-ol. Similar reactions in literature have certain risks, long routes and low yields. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, and suitable for the overall yield. Summary of the invention [0003] The purpose of the present invention is to develop a method for synthesizing 4-(aminomethyl)chroman-3-ol with easily available raw materials, convenient operation, easy reaction control, and high yield. It mainly solves the technical problems that are currently not suitable for industrial synthesis methods. [0004] The technical scheme of the pr...

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Application Information

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IPC IPC(8): C07D311/58
CPCC07D311/58
Inventor 何燕平任文武周强刘胜攀汪冬冬刘月领徐富军焦家盛安自强王瑞琪余沛东张莉莉陈佩于凌波马汝建
Owner 上海合全医药有限公司
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