Preparation method of tertiary butyl-1-methyl-5-oxysub unit triazaspiro[5.5] undecane-8-formyl ester

A triazaspiro, oxygen subunit technology, applied in the direction of organic chemistry and the like, can solve the problem of no suitable industrial synthesis method, etc., and achieve the effects of short synthesis route, easy reaction and low system temperature

Inactive Publication Date: 2019-03-19
WUXI APPTEC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Preparation method of tertiary butyl-1-methyl-5-oxysub unit triazaspiro[5.5] undecane-8-formyl ester
  • Preparation method of tertiary butyl-1-methyl-5-oxysub unit triazaspiro[5.5] undecane-8-formyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: a. Dissolve ethylenediamine (18.1g, 0.3mol) and benzyltriethylammonium chloride (2.86g, 0.012mol) in dichloromethane (200 mL), and lower the temperature of the reaction system to After 5°C, add sodium hydroxide (100g, 2.51mol) in water (150mL) solution dropwise, keep the system temperature at 5°C and stir for 1.5 hours; after the system temperature rises to 10°C, add N-Boc-3-piper Pyridone (50g, 0.25mol) and chloroform (44.94g, 0.37mol) were dissolved in dichloromethane (200mL) and added dropwise to the reaction system. During the whole process, the temperature of the system was controlled at 15°C, and the reaction was stirred for 0.5 hours. TLC (2 Chloromethane / methanol volume ratio=10 / 1) shows the end of the reaction.

[0011] b. Reduce the temperature of the reaction system to 10°C and add water to quench it. After 0.5 hours, separate the organic phase and wash it with salt water. Anhydrous Na 2 SO 4 As a drying agent, filter and concentrate under reduce...

Embodiment 2

[0014] Example 2: a. Dissolve ethylenediamine (181g, 3mol) and benzyltriethylammonium chloride (28.6g, 0.12mol) in dichloromethane (1000 mL), and lower the temperature of the reaction system to 5°C Then start to add sodium hydroxide (1000g, 2.51mol) solution in water (1500mL) dropwise, keep the system temperature at 5°C and stir for 1.5 hours; after the system temperature rises to 15°C, add N-Boc-3-piperidone ( 500g, 2.5mol) and chloroform (449.4g, 3.7mol) were dissolved in dichloromethane (2000mL) and added dropwise to the reaction system. During the whole process, the temperature of the system was controlled at 15°C, and the reaction was stirred for 0.5 hours. TLC (dichloromethane / Methanol volume ratio=10 / 1) shows the end of the reaction.

[0015] b. Reduce the temperature of the reaction system to 10°C and add water to quench it. After 0.5 hours, separate the organic phase and wash it with salt water. Anhydrous Na 2 SO 4 As a drying agent, filter and concentrate under re...

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PUM

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Abstract

The invention relates to a preparation method of tertiary butyl-1-methyl-5-oxysub unit triazaspiro[5.5] undecane-8-formyl ester and primarily solves the technical problem that proper industrial synthetic methods are not available in the prior art. The preparation method comprises two steps: S1, adding ethanediamine and benzyl triethyl ammonium chloride by taking dichloromethane as a solvent, reducing the temperature of a reaction system to 5 DEG C and dropwise adding an aqueous solution of sodium hydroxide, stirring the mixture to react, dissolving N-Boc-3-piperidone and chloroform in dichloromethane into the reaction system when the temperature of the system is raised to 10 DEG C, and stirring the mixture to react when the reaction temperature is 15 DEG C to obtain a compound 3; and S2, dissolving the compound 3 in methanol at room temperature, adding formaldehyde and acetic acid, reducing the temperature of the reaction system to 0 DEG C, adding sodium cyanoborohydride, and carryingout a reaction at 20 DEG C and carrying out purification treatment to obtain a final product. The compound obtained by the invention provides an important intermediate for synthesizing many drugs.

Description

technical field [0001] The present invention relates to the preparation method of tert-butyl-1-methyl-5-oxyethylene triazaspiro[5.5]undecane-8-carboxylate, i.e. tert-butyl-1-methyl-5-oxo Preparation method of subunit-1,4,8-triazaspiro[5.5]undecane-8-carboxylate (CAS: 1160247-11-9). Background technique [0002] tert-butyl-1-methyl-5-oxyylidene-1,4,8-triazaspiro[5.5]undecane-8-carboxylate and its derivatives are widely used in medicinal chemistry and organic synthesis application. At present, there are few reports on the synthesis of tert-butyl-1-methyl-5-oxylidene-1,4,8-triazaspiro[5.5]undecane-8-carboxylate, and there are some similar literature reactions. The risk and the route are long, and the yield is low. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 李庆攀周强任文武李红何米娜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 WUXI APPTEC
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