A kind of preparation method of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazol-7-yl)methanol
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A technology of tetrahydropyran and 4-c, which is applied in the direction of organic chemistry, can solve the problems of no suitable industrial synthesis method, and achieve the effects of short synthesis route, easy reaction and convenient operation
Active Publication Date: 2021-05-18
上海药明康德新药开发有限公司 +1
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Mainly solve the technical problem that there is no suitable industrial synthesis method at present
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Embodiment 1
[0012] Example 1: a, boron trifluoride ether (334 g, 2.24 mol) was slowly added dropwise into the mixture of compound 1 (172.6 g, 1.12 mol) and triethyl orthoformate (334 g, 2.24 mol), and the reaction The reaction was continued for 2 hours at room temperature (20-30°C). The reaction solution was added into saturated aqueous sodium bicarbonate solution, and after the reaction was quenched, it was extracted with dichloromethane. The organic phase was concentrated by distillation under reduced pressure to obtain the crude product 2 (380.0 g, 86.7%) in the form of black oil, which was directly used in the next reaction.
[0013] b. Dissolve compound 2 (380.0 g, 2.03 mol) and acetic acid (5 ml) in methanol (1.5 L), control the reaction temperature at 80 ° C, then add benzylhydrazine (200 g, 1.025 mol). The controlled reaction was continued at 80°C for 10 hours. The reaction solution was added to a saturated aqueous solution of sodium bicarbonate, then concentrated by distillati...
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Abstract
The invention relates to a preparation method of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazol-7-yl)methanol, which mainly solves the technical problem that there is no suitable industrial synthesis method at present. The present invention is divided into ten steps: first, compound 1 and triethyl orthoformate generate compound 2 under the action of boron trifluoride ether, then react with benzylhydrazine to obtain compound 3, and react with acetyl chloride to obtain compound 4, then obtain compound 4 in two Add N-bromosuccinimide to the solution of methyl chloride to obtain compound 5, react with ethylene boron trifluoride potassium salt to obtain compound 6, and obtain compound 7 with sodium hydroxide, and obtain compound 7 with N-bromosuccinimide Compound 8 was obtained by the reaction, compound 9 was obtained under the action of methanesulfonic acid, compound 10 was obtained by reacting with silver nitrate in acetonitrile solution, and product 11 was obtained by reacting with hydrogen gas under the catalyst palladium carbon. The compounds obtained in the present invention are useful intermediates or products of many pharmaceutical synthesis.
Description
[0001] technology field [0002] The present invention relates to a synthesis method of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazol-7-yl)methanol (CAS: 1422344-20-4). Background technique [0003] (2,4,5,7-Tetrahydropyrano[3,4-c]pyrazol-7-yl)methanol and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthesis of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazol-7-yl)methanol, and similar literature reactions have certain risks and long routes. The rate is lower. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0004] The purpose of the present invention is to develop a kind of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazole-7 with easy to obtain raw materials, convenient operation, easy to control reaction and high yield. -base) the synthetic method of methanol. It mainly ...
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