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Synthesis method of tertiary butyl-9-oxo-2,5,8-triazaspiro[3.5] nonane-2-carboxylate

A technology of a triazaspiro and a synthetic method, which is applied in the field of synthesis of tert-butyl-9-oxygenide-2,5,8-triazaspiro[3.5]nonane-2-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 strong repeatability

Inactive Publication Date: 2019-04-12
上海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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  • Synthesis method of tertiary butyl-9-oxo-2,5,8-triazaspiro[3.5] nonane-2-carboxylate
  • Synthesis method of tertiary butyl-9-oxo-2,5,8-triazaspiro[3.5] nonane-2-carboxylate

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Embodiment 1

[0011] Ethylenediamine (5.27 g, 87.62 mmol, 5.86 mL) and benzyltriethylammonium chloride (665.20 mg, 2.92 mmol) were dissolved in chloroform (50.00 mL), and compound 1 (10.00 g, 58.41 mmol , 1.00 eq), and controlled the temperature at 0-10 °C, dissolved sodium hydroxide (11.68 g, 292.05 mmol, 5.00 eq) in water (11.68 mL), added dropwise to the above chloroform (50.00 mL) solution, and Control the temperature below 10°C, and then react at 25°C for 16 hours. After the reaction was complete, the organic layer was separated, the aqueous phase was extracted three times with chloroform, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was separated and purified by column chromatography to obtain compound 2 as a white solid (5.6 g). Yield: 41 %. 1 HNMR: CDCl3 Varian_Y_400MHz, δ=4.363 (d, 2H), 3.656 (d, 2H), 3.362 (t, 2H), 3.012 (t, 2H), 1.417 (s, 9H).

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Abstract

The invention relates to a synthesis method of compound tertiary butyl-9-oxo-2,5,8-triazaspiro[3.5] nonane-2-carboxylate. It mainly solves the technical problem that there is no suitable method for industrial synthesis at present. Technical scheme of the invention is that the synthesis method of the compound tertiary butyl-9-oxo-2,5,8-triazaspiro[3.5] nonane-2-carboxylate, the final compound 2 canbe obtained in one step of the invention, ethylenediamine and benzyl(triethyl)ammonium chloride are dissolved in chloroform, the compound 1 is added under stirring, and the temperature is controlledat 0-10 DEG C, sodium hydroxide is dissolved in water and added dropwise to chloroform solution, and then reacted at 25 DEG C for 16 hours to obtain the compound 2. The reaction formula is described in the description.

Description

technical field [0001] The invention relates to a synthesis method of the compound tert-butyl-9-oxyethylene-2,5,8-triazaspiro[3.5]nonane-2-carboxylate. Background technique [0002] The compound tert-butyl-9-oxyylidene-2,5,8-triazaspiro[3.5]nonane-2-carboxylate (CAS: 1251002-03-5 ) and related derivatives are widely used in medicinal chemistry and Widely used in organic synthesis. 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 the present invention is to develop a kind of tert-butyl-9-oxygenidene-2,5,8-triazaspiro[3.5]nonane which has easy-to-get raw materials, easy operation, easy-to-control reaction and high yield - Synthetic method of 2-formyl ester. It mainly solves the technical problem that there is no suitable industrial synthesis method at present. [...

Claims

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Application Information

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IPC IPC(8): C07D487/10
CPCC07D487/10
Inventor 何米娜周强任文武李红李庆攀蒋欣欣吴东平何华敬安自强刘月领吴艳何燕平焦家盛于凌波马汝建
Owner 上海药明康德新药开发有限公司
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