A preparation method of 4,5-dihydro-1h,3h-pyrrolo[1,2-a][1,4]diazepine-2,4-dicarboxylate-2-tert-butyl ester
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A technology of diazepine and tert-butyl ester, which is applied in the field of preparation of dihydropyrrolodiazepine dicarboxylate-2-tert-butyl ester, can solve the problems of no suitable industrial synthesis method, and achieve a synthetic route Short, easy-to-response, and easy-to-operate effects
Active Publication Date: 2021-11-09
CHANGZHOU HEQUAN PHARMA CO LTD
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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
[0010] Example 1: a. Dissolve compound 1 (100.00 g, 1.05 mol) in acetonitrile (500 mL), add potassium carbonate (218.00 g, 1.58 mol) and stir for half an hour, then slowly add compound 2 dropwise at 0°C, after the dropwise addition is completed The reaction was stirred at 20°C for 12 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. Water was added to the reaction system, and then extracted three times with ethyl acetate. The combined organic phases were purified by silica gel column chromatography to obtain compound 3 (186.83 g, 901.56 mmol), with a yield of 85.86%.
[0011] b. Dissolve compound 3 (186.83 g, 901.56 mmol) and benzylamine (106.26 g, 991.71 mmol) in ethanol (500 mL), react at 20°C for half an hour, then add sodium borohydride (20.46 g, 540.94 mmol) at 20 °C stirring was continued for 30 minutes. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1) showed that the starting material was consumed completely. The r...
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Abstract
The present invention relates to a kind of 4,5-dihydro-1H,3H-pyrrolo[1,2-A][1,4]diazepine-2,4-dicarboxylic acid-2-tert-butyl ester The preparation method mainly solves the technical problem that there is no suitable industrial synthesis method at present. The present invention is divided into five steps. First, compound 1 is dissolved in acetonitrile and reacts with compound 2 at room temperature under the action of potassium carbonate to generate compound 3. The second step is the reductive amination of compound 2 and benzylamine in ethanol by adding sodium borohydride and simultaneous ring closure to obtain compound 4. Then in compound 4 ethanol solution, add 10% palladium carbon hydrogen to remove the benzyl protecting group of compound 4 to obtain compound 5, then in compound 5 methanol solution, pass through and BOC 2 O is reacted to obtain compound 6, and finally compound 6 is hydrolyzed by adding sodium hydroxide in a mixed solvent of methanol and water to obtain final product 7. The compound obtained in the present invention is a useful intermediate or product for the synthesis of many medicines.
Description
technical field [0001] The present invention relates to a preparation method of dihydropyrrolodiazepine dicarboxylic acid-2-tert-butyl ester, that is, 4,5-dihydro-1H,3H-pyrrolo[1,2-A][1, 4] Synthesis method of diazepine-2,4-dicarboxylate-2-tert-butyl ester (CAS: 1251017-62-5). Background technique [0002] 4,5-Dihydro-1H,3H-pyrrolo[1,2-A][1,4]diazepine-2,4-dicarboxylic acid-2-tert-butyl ester and related derivatives in It is widely used in medicinal chemistry and organic synthesis, and is an important class of pharmaceutical intermediates. At present, there are few reports on the synthesis of 4,5-dihydro-1H,3H-pyrrolo[1,2-A][1,4]diazepine-2,4-dicarboxylic acid-2-tert-butyl ester. Few, similar literature reaction route is long, and yield is low, is not suitable for factory scale-up production. 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 t...
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