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Method for quickly preparing cis-octahydropyrrolo[3,2-b]pyrrole

A technology of octahydropyrrole and 2-b, which is applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of harsh reaction conditions, inconvenient reaction operation, long reaction route, etc., achieve short reaction time, reasonable reaction process selection, Conducive to the effect of process amplification

Inactive Publication Date: 2011-06-08
上海药明康德新药开发有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to provide a method for rapidly preparing cis-octahydropyrrolo[3,2-b]pyrrole, which mainly solves the problems in the existing cis-octahydropyrrolo[3,2-b]pyrrole preparation process. The raw materials are expensive, the reaction conditions are harsh, the reaction route is long, the reaction operation is inconvenient, and the ring closure produces a large number of isomers.

Method used

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  • Method for quickly preparing cis-octahydropyrrolo[3,2-b]pyrrole

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Embodiment 1

[0015] Compound 1 (10.0 g, 45.6 mmol), allyl bromide (7.9 g, 137 mmol), p-toluenesulfonic acid (11.8 g, 68.4 mmol) and anhydrous sodium sulfate (25.1 g) were added into xylene (200 mL) . The reaction mixture was heated to reflux and stirred for 20 hours. The reactant was cooled and filtered. After the filtrate was concentrated, Compound 2 (6.1 g) was obtained as a yellow oil with a yield of 53.2%.

[0016] To a solution of compound 2 (10.5 g, 40.6 mmol) in methanol (100 mL) was added ammonium acetate (31.2 g, 405 mmol). The reaction mixture was heated to reflux for 1 hour and then cooled to 30°C. Sodium cyanoborohydride (10.2 g, 162 mmol) was added in portions. The reaction mixture was heated to reflux for 1 hour. After the reaction was cooled, ice water (50 mL) was added to quench the reaction. Extracted with ethyl acetate (3x50 mL). The organic phase was extracted with 4N hydrochloric acid solution (3x50mL), the aqueous phase was washed with diethyl ether (100mL), sodi...

Embodiment 2

[0020] Compound 1 (10.0 g, 45.6 mmol), allyl chloride (7.9 g, 137 mmol), benzenesulfonic acid (11.8 g, 68.4 mmol) and anhydrous magnesium sulfate (25.1 g) were added to toluene (200 mL). The reaction mixture was heated to reflux and stirred for 20 hours. The reactant was cooled and filtered. After the filtrate was concentrated, Compound 2 (5.83 g) was obtained as a yellow oil with a yield of 50.2%.

[0021] To a solution of compound 2 (10.5 g, 40.6 mmol) in ethanol (100 mL) was added ammonium acetate (31.2 g, 405 mmol). The reaction mixture was heated to reflux for 1 hour and then cooled to 30°C. Sodium acetate borohydride (10.2 g, 162 mmol) was added portionwise. The reaction mixture was heated to reflux for 1 hour. After the reaction was cooled, ice water (50 mL) was added to quench the reaction. Extracted with ethyl acetate (3x50 mL). The organic phase was extracted with 4N hydrochloric acid solution (3x50mL), the aqueous phase was washed with diethyl ether (100mL), so...

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Abstract

The invention relates to a novel synthesis method for cis-octahydropyrrolo[3,2-b]pyrrole, and mainly solves the technical problems that raw materials are expensive, reaction conditions are harsh, a reaction route is long, the reaction operation is inconvenient, and a large number of isomers are generated through ring closure in the conventional cis-octahydropyrrolo[3,2-b]pyrrole preparation process. The method comprises the following steps of: performing alkylation reaction of industrially available 3-pyrrolidone serving as an initiative raw material and an allyl compound directly under the action of acid to obtain a 3-tetrahydro-pyrrolidone substitute; performing reductive amination reaction to obtain a 3-aminopyrrolidine derivative; performing protective group adding reaction; and performing ozonization reduction ring-closing reaction and dehydroxylation reaction on the 3-aminopyrrolidine derivative added with the protective group to obtain a corresponding cis-octahydropyrrolo[3,2-b]pyrrole derivative. The target product and important intermediates can be widely applied to synthesizing various pyrrole derivatives.

Description

technical field [0001] The present invention relates to a new synthesis method of cis-octahydropyrrolo[3,2-b]pyrrole. Background technique [0002] Cis-octahydropyrrolo[3,4-b]pyrrole ring compounds and their corresponding derivatives are widely used as important intermediates for the synthesis of adenosinase inhibitors 4-quinoline carboxylic acids, and for the synthesis of urine Pyrimidine-based structure, selectively inhibits type III DNA polymerase and type II topoisomerase antibacterial compound. For example: the latest research found that a new class of 2-aryl-7-amino-substituted-oxazolo[5,4-b]pyrimidines is a very effective parent structure adenosinase inhibitor. As shown in formula 1, from the X-ray study of the molecular structure, it is found that its activity is closely related to the spatial geometry of the molecule with the appropriate ditetrahydropyrrole ring structure in the 7-position ammonia substitution group. The compound can have a certain The space activ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCY02P20/55
Inventor 毕增梁王瑞乐俞鸿斌罗彤马汝建
Owner 上海药明康德新药开发有限公司
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