Synthesis method of ethyl-3-oxo-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate

A synthesis method and oxygen subunit technology, applied in the direction of organic chemistry, etc., can solve the problem of not being suitable for industrial synthesis methods, etc., and achieve the effects of reasonable reaction process design, convenient operation and easy reaction.

Pending Publication Date: 2020-09-15
SHANGHAI STA PHARMA R&D CO LTD +1
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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 ethyl-3-oxo-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate
  • Synthesis method of ethyl-3-oxo-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate

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Embodiment

[0012] Step 1: Dissolve compound 1 (75.0 g, 0.375 mol) and triethylamine (41.6 g, 0.412 mol) in dichloromethane (1.0 L), slowly add chloroacetyl chloride (42.0 g, 0.375 mol ), the reaction was kept stirring at room temperature for 2 hours. High performance liquid chromatography showed that the starting material was completely reacted. The reaction was quenched by the addition of saturated aqueous sodium carbonate. The two phases are separated. The organic phase was washed with brine, dried by adding anhydrous sodium sulfate, and spin-dried to obtain compound 2 as a yellow solid (95.0 g, purity: 91%).

[0013] Step 2: Compound 2 (95 g, 0.34 mol) was dissolved in acetone (1.0 L), and sodium iodide (153 g, 1.02 mol) was added at room temperature, and the reaction was stirred at 50°C under reflux for 4 hours. TLC showed the starting material was completely reacted. The reaction solution was cooled to room temperature, filtered, and the filtrate was spin-dried in vacuo to obtai...

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Abstract

The invention relates to a synthesis method of ethyl-3-oxo-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate. The synthesis method mainly solves the technical problem that no suitable industrial synthesis method exists at present. The method comprises the following three steps: 1, adding triethylamine and chloroacetyl chloride into a solvent dichloromethane of a compound 1, and reacting to obtain a compound 2; 2, reacting the compound 2 with sodium iodide in acetone to obtain a compound 3; and 3, reacting the compound 3 with potassium tert-butoxide in tert-butyl alcohol and tetrahydrofuran to obtaina final compound 4. The reaction formula is shown in the specification.

Description

technical field [0001] The invention relates to a synthesis method of the compound ethyl-3-oxygenide-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate. Background technique [0002] The compound ethyl-3-oxylidene-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate (CAS: 1422344-43-1) and related derivatives are used in medicinal chemistry and Widely used in organic synthesis. Currently, there are few reports on the synthesis methods of ethyl-3-oxylidene-1-oxa-4-azaspiro[5.5]undecane-9-carboxylate. 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 is to develop a kind of raw material that is easy to get, easy to operate, easy to control the reaction, higher yield of ethyl 3-oxygenide-1-oxa-4-azaspiro[5.5]undecane- Synthetic method of 9-formyl ester. It mainly sol...

Claims

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Application Information

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IPC IPC(8): C07D265/36
CPCC07D265/36
Inventor 张大为周强高明飞姚宝元兰倩倩赵廷王曦卫维魏昕睿谭汝鹏贾涛白有银孙春付新雨于凌波马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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