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Synthetic method for tert-butyl 1,10-dioxo-2,7-diazaspiro[4.5]decane-7-carboxylate

A technology of tert-butyl formate and dioxyylidene, applied in the field of synthesis of 1,10-dioxylidene-2,7-diazaspiro[4.5]decane-7-tert-butyl carboxylate, capable of Solve the problems of no suitable industrial synthesis methods, etc., and achieve the effects of reasonable reaction process design, easy reaction and convenient operation

Inactive Publication Date: 2019-04-12
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Application Information

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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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  • Synthetic method for tert-butyl 1,10-dioxo-2,7-diazaspiro[4.5]decane-7-carboxylate
  • Synthetic method for tert-butyl 1,10-dioxo-2,7-diazaspiro[4.5]decane-7-carboxylate

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Embodiment

[0012] The first step: 1-tert-butyl-3-ethyl-4-oxyylidene piperidine-1,3-dicarboxylate (300 g, 1.11 mol) and bromoacetonitrile (145.90 g, 1.22 mol) were dissolved into acetone (1.5 L), and then potassium carbonate (244.51 g, 1.77 mol, 1.6 eq) was added to the reaction system and maintained at 25°C for 12 hours. TLC (petroleum ether / ethyl acetate volume ratio = 2 / 1) showed that the reaction was complete. The crude product obtained by concentrating the reaction solution under reduced pressure was dissolved in 1L of water and 1.5L of ethyl acetate, and then extracted with ethyl acetate (1L x 3), the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product , the resulting crude product was purified with silica gel column (gradient elution: petroleum ether / ethyl acetate~petroleum ether / ethyl acetate volume ratio=10:1~2:1) to obtain colorless oily compound 2 (300g crude product), yield It was 87.42%.

[0013] 1H NMR: ...

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Abstract

The invention relates to a synthetic method for tert-butyl 1,10-dioxo-2,7-diazaspiro[4.5]decane-7-carboxylate, and mainly solves the technical problem that the tert-butyl 1,10-dioxo-2,7-diazaspiro[4.5]decane-7-carboxylate has no synthetic method suitable for industrialization. The synthetic method comprises the following four steps: step 1, dissolving a compound 1 and bromoacetonitrile into anhydrous acetone, and adding potassium carbonate into the above reaction system to obtain a compound 2; step 2, performing a reaction on the compound 2 under the action of sodium borohydride to obtain a compound 3; step 3, introducing hydrogen, and performing ring closing on the compound 3 under the catalytic effect of nickel to obtain a compound 4; and step 4, performing oxidation on the compound 4 toobtain a compound 5, wherein a reaction formula is shown in the description.

Description

technical field [0001] The invention relates to a synthesis method of compound 1,10-dioxylidene-2,7-diazaspiro[4.5]decane-7-carboxylic acid tert-butyl ester. Background technique [0002] Compound 1,10-dioxylidene-2,7-diazaspiro[4.5]decane-7-carboxylate tert-butyl ester (PubChemCompound ID: 131217523) and related derivatives are widely used in medicinal chemistry and organic synthesis application. Currently, there are few reports on the synthesis of tert-butyl 1,10-dioxylidene-2,7-diazaspiro[4.5]decane-7-carboxylate. Nagata, Toshiaki et al published a similar literature Tetrahedron Letters (Tetrahedron Letters) 2001, vol. 42, # 47, p. 8345 – 8349, and others mentioned the synthetic route of benzenesulfonyl protection. However, the literature route is long, the raw materials are not easy to obtain, and it is completely unsuitable for industrial production. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 张大为周强白有银高明飞付新雨姚宝元谭汝鹏孔祥南刘鲜赵廷王曦孙春卢荣昌刘雨雷魏昕睿于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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