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Preparing method of canrenone important intermediate

The technology of an intermediate and canrenone, which is applied in the field of preparation of important intermediates of canrenone, can solve the problems of poor selectivity, reduced product yield, and high impurity content, and achieves low equipment requirements, reduced by-products, and simple operation requirements. Effect

Active Publication Date: 2018-05-18
GUANGXI WANDE PHARMA
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Problems solved by technology

[0010] The technical problem to be solved by this invention is to provide the preparation method of the important intermediate of canrenone, to overcome the existing dehydrogenation reaction process in the prior art when using tetrachlorocyanoquinone and dichlorodicyanobenzoquinone as reducing agent, due to Its selectivity is poor, and impurity compound Ⅲ and compound Ⅳ are generated, resulting in higher impurity content and lower product yield

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preparation example Construction

[0036] The preparation method of the important intermediate of canrenone is prepared to obtain compound II, and the chemical reaction equation involved is as follows:

[0037]

Embodiment 1

[0039] like figure 1 The preparation method of the important intermediate of canrenone comprises the following steps: add 30g of compound I, 100ml of toluene, 200ml of acetone, 30ml of phosphate buffer (pH=10) into a three-neck flask, cool down to -80°C, and slowly add 60g of dichlorodicyanobenzoquinone, keep warm for 3h, TLC (PE:EA=4:1) shows that the reaction is complete (no compound I spots), add 60ml of 5% sodium hydroxide solution, stir for 2h, suction filter, rinse with water When the filtrate is neutral, take out the filter cake and dry it.

[0040] Obtain product 26.4g, yield 88%, such as figure 2 The purity of the product is 98.1%, and the contents of impurity 1 (compound III) and impurity 2 (compound IV) are 0.16% and 0.61%, respectively.

Embodiment 2

[0042] like figure 1 The preparation method of the important intermediate of canrenone comprises the following steps: add 50g of compound I, 100ml of toluene, 150ml of acetone, 5ml of phosphate buffer (pH=8) into a three-neck flask, cool to -30°C, and slowly add 25g of dichlorodicyanobenzoquinone was incubated at -30°C for 1 hour. TLC (PE:EA=4:1) showed that the reaction was complete (no compound I spots), and 1000ml of 1% sodium hydroxide solution was added and stirred for 1 hour. Suction filtration, rinse with water until the filtrate is neutral, take out the filter cake, and dry.

[0043] 43.5 g of the product was obtained with a yield of 87% and a purity of 97.8%. The contents of impurity 1 (compound III) and impurity 2 (compound IV) were 0.22% and 0.79%, respectively.

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Abstract

The invention provides a preparing method of a canrenone important intermediate. The preparing method comprises the following steps of 1, adding a first compound into a reaction container, adding a mixing solvent and a buffer solution, cooling to minus 80 DEG C to minus 30 DEG C, slowly adding 2,3-dicyano-5,6-dichlorobenzoquinone, conducting a reaction at minus 80 DEG C to minus 30 DEG C for 1-3 h, after the reaction is finished, adding alkaline liquor to end the reaction and conducting aftertreatment to obtain a second compound. By means of the preparing technology, due to the use of the buffer solution, the defects existing in the prior art that in the dehydrogenation reaction process, when tetrachlorohydroquinone and 2,3-dicyano-5,6-dichlorobenzoquinone are used as reducing agent, sincetetrachlorohydroquinone and 2,3-dicyano-5,6-dichlorobenzoquinone have poor selectivity, a impurity third compound and fourth compound are generated, a product is high in impurity content, and the yield is low are overcome.

Description

technical field [0001] The invention belongs to the field of medicine manufacture, and in particular relates to a preparation method of an important intermediate of canrenone. Background technique [0002] Canrenone, chemically named 17β-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid-Y-lactone, is a commonly used diuretic and is also a synthetic aldosterone An important intermediate of the receptor antagonist spironolactone. Canrenone can also be widely used in the preparation of important steroid raw materials such as eplerenone and other cardiovascular disease drugs. Compound II is an important intermediate in the production process of canrenone. Its synthesis method has been reported in the literature to use tetrachlorocyanoquinone and dichlorodicyanobenzoquinone as reducing agents. Because of its poor selectivity, the following side reactions occur: [0003] [0004] At the same time, dichlorodicyanobenzoquinone reacts to generate acidic DDHQ, which hydrolyze...

Claims

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Application Information

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IPC IPC(8): C07J21/00
CPCC07J21/00
Inventor 蒋青锋李家宝
Owner GUANGXI WANDE PHARMA
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