Preparation method of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazole-7-yl)methanol
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A technology of tetrahydropyran, 4-c, applied in directions such as organic chemistry, can solve problems such as no suitable industrial synthesis method, and achieve the effects of short synthesis route, easy reaction and convenient operation
Active Publication Date: 2019-11-22
上海药明康德新药开发有限公司 +1
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[0011] Example 1: a. Add boron trifluoride ether (334 g, 2.24 mol) slowly and dropwise into the mixture of compound 1 (172.6 g, 1.12 mol) and triethyl orthoformate (334 g, 2.24 mol), and react The solution continues to react for 2 hours at room temperature (20-30°C). The reaction solution was added to saturated sodium bicarbonate aqueous solution, and after the reaction was quenched, it was extracted with dichloromethane. The organic phase was concentrated by distillation under reduced pressure to obtain a black oily crude product 2 (380.0 g, 86.7%), which was directly used in the next reaction.
[0012] 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, and then add benzylhydrazine (200 L) dissolved in methanol (0.5 L). g, 1.025 mol). The reaction was controlled to continue at 80°C for 10 hours. The reaction solution was added to saturated sodium bicarbonate aqueous solution, and then concentrated u...
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Abstract
The invention relates to a preparation method of (2,4,5,7-tetrahydropyrano[3,4-c]pyrazole-7-yl)methanol, and mainly solves the technical problem that no suitable industrial synthesis method exists atpresent. The method comprises ten steps in total: firstly, generating a compound 2 from a compound 1 and triethyl orthoformate under the action of boron trifluoride ethyl ether; performing a reactionwith benzyl hydrazine to obtain a compound 3; performing a reaction with acetyl chloride to obtain a compound 4; then, adding N-bromosuccinimide into a dichloromethane solution to obtain a compound 5;performing a reaction with ethylene boron trifluoride potassium salt to obtain a compound 6; performing a reaction with sodium hydroxide to obtain a compound 7; performing a reaction on the compound7 with N-bromosuccinimide to obtain a compound 8; preparing a compound 9 under the action of methanesulfonic acid; performing a reaction on the compound 9 with silver nitrate in an acetonitrile solution to obtain a compound 10; and finally performing a reaction on the compound 10 with hydrogen under the action of a catalyst palladium-carbon to obtain the product 11. The compounds obtained in the invention are useful intermediates or products for synthesis of many drugs.
Description
technical field [0001] 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 [0002] (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 [0003] 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 solves t...
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