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Method for preparing 5-(tert-butoxycarbonyl)-2-oxooctahydropyrrolo[3, 4-b]pyrrole-3a-carboxylic acid

A kind of technology of oxyethylene octahydropyrrole and tert-butoxycarbonyl, which is applied to the preparation method of 5-tert-butoxycarbonyl-2-oxygenide octahydropyrrolo[3,4-b]pyrrole-3a-carboxylic acid It can solve the problems such as the lack of suitable industrial synthesis methods, and achieve the effects of reasonable reaction process design, easy reaction and cost saving.

Inactive Publication Date: 2019-03-22
武汉药明康德新药开发有限公司
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Method for preparing 5-(tert-butoxycarbonyl)-2-oxooctahydropyrrolo[3, 4-b]pyrrole-3a-carboxylic acid

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Embodiment 1

[0012] Compound 1 (100 g, 38.9 mmol), ethyl bromoacetate (130 g, 0.78 mol) and tetrabutylammonium fluoride (122 g, 0.47 mol) were dissolved in 1500 mL tetrahydrofuran at 25°C, and stirred at 25°C for 12 Hours, after the reaction was over, the reaction solution was spin-dried, and the obtained crude product was dissolved in 3000 mL of ethyl acetate, washed three times with water, dried and spin-dried, and column chromatography obtained 74 g of compound 2 as a yellow oil, yield: 56%. H NMR: CDCl3 400MHz δ 1.22-1.29 (m, 6H), 1.5 (s, 9 H), 2.96-3.08 (m 1H), 3.57-3.60 (m, 1H), 3.91-4.00 (m, 2H), 4.08-4.32 (m, 6H).

[0013] Compound 2 (30 g, 87.4 mmol), hydroxylamine hydrochloride (9.1 g, 131.1 mmol) and sodium bicarbonate (11 g, 131.1 mmol) were dissolved in a mixed solvent of 150 ml tetrahydrofuran and 300 mL ethanol, and stirred at 25 °C for 12 Hour. After the reaction, ethanol and tetrahydrofuran were spin-dried, and the obtained crude product was dissolved in 1000 mL of ethyl...

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Abstract

The invention relates to a method for synthesizing (3aS, 6aR)-5-(tert-butoxycarbonyl)-2-oxooctahydropyrrolo[3, 4-b]pyrrole-3a-carboxylic acid, and mainly solves a technical problem of absence of a method suitable for industrial synthesis at present. The method provided by the invention comprises the following four steps: step one, dissolving a compound 1, ethyl bromoacetate and tetrabutylammoniumfluoride in tetrahydrofuran to obtain a compound 2; step two, dissolving the compound 2, hydroxylamine hydrochloride and sodium bicarbonate in a mixed solvent of tetrahydrofuran and ethanol to obtaina compound 3; step three, adding the compound 3, Raney nickel and ammonia water into ethanol, filtering and spin-drying to obtain a compound 4 after finishing reaction; and step four, adding the compound 4 and sodium ethoxide into ethanol, performing reflux reaction to obtain a white solid compound 5, namely, (3aS, 6aR)-5-(tert-butoxycarbonyl)-2-oxooctahydropyrrolo[3, 4-b]pyrrole-3a-carboxylic acid.

Description

technical field [0001] The present invention relates to the preparation method of compound 5-tert-butoxycarbonyl-2-oxyylidene octahydropyrrolo[3,4-b]pyrrole-3a-carboxylic acid, namely (3aS,6aR)-5-(tert-butoxy Carbonyl)-2-oxylidene octahydropyrrolo[3,4-b]pyrrole-3a-carboxylic acid synthesis method. Background technique [0002] Compound (3aS,6aR)-5-(tert-butoxycarbonyl)-2-oxylideneoctahydropyrrolo[3,4-b]pyrrole-3a-carboxylic acid (CAS: 1251013-32-7) and related Derivatives are widely used in medicinal chemistry and organic synthesis. Currently, there is no literature report on the industrial synthesis of (3aS,6aR)-5-(tert-butoxycarbonyl)-2-oxylidene octahydropyrrolo[3,4-b]pyrrole-3a-carboxylic acid. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of this invention i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07B2200/07C07D487/04
Inventor 李红周强任文武何米娜蒋欣欣吴东平李庆攀何华敬安自强刘月领吴艳何燕平焦家盛于凌波马汝建
Owner 武汉药明康德新药开发有限公司
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