Preparation method of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid

An azaspirane, tert-butyl technology, applied in 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2 , The field of preparation of 7-dicarboxylic acid can solve the problems of no suitable industrial synthesis method, and achieve the effects of saving purification time and consumption, easy reaction and convenient operation

Inactive Publication Date: 2017-06-13
SHANGHAI SYNTHEALL PHARM CO LTD
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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 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid
  • Preparation method of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid
  • Preparation method of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid

Examples

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Embodiment 1

[0010] Example 1: a. Compound 1 (430g, 1.77mol) was dissolved in 3L of tetrahydrofuran, under the protection of nitrogen, the reaction temperature was controlled at -78°C to -50°C, and n-butyllithium (125g, 1.95 mol). After the dropwise addition, the reaction temperature was maintained and stirring was continued for 1-2 hours. Benzyl chloroformate (322.8 g, 1.86 mol) was dissolved in 1 L of tetrahydrofuran, and the reaction temperature was controlled at -78°C to -50°C, and added dropwise to the reaction solution. After the dropwise addition, the reaction temperature was maintained and stirring was continued for 2-4 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. The reaction solution was poured into saturated aqueous ammonium chloride (5 L), and extracted with ethyl acetate (3 L x 3). The organic phases were combined, dried over sodium sulfate, filtered, and concentrated by distillation under reduced pressure to obtain a cr...

Embodiment 2

[0015] Example 2: a. Compound 1 (4300g, 17.7mol) was dissolved in 25L of tetrahydrofuran, under the protection of nitrogen, the reaction temperature was controlled at -78°C to -50°C, and n-butyllithium (1250g, 19.5 mol). After the dropwise addition, the reaction temperature was maintained and stirring was continued for 1-2 hours. Benzyl chloroformate (3228 g, 18.6 mol) was dissolved in 5 L of tetrahydrofuran, and the reaction temperature was controlled at -78°C to -50°C, and added dropwise to the reaction solution. After the dropwise addition, the reaction temperature was maintained and stirring was continued for 2-4 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. The reaction solution was poured into saturated aqueous ammonium chloride solution (35 L), and extracted with ethyl acetate (15 L x 3). The organic phases were combined, dried over sodium sulfate, filtered, and concentrated by distillation under reduced pressure t...

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Abstract

The invention relates to a synthesis method of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid, aiming at mainly solving the technical problem that a suitable industrial synthesis method does not exist at present. The synthesis method is divided into four steps as follows: firstly, taking a compound 1 to react with n-butyl lithium and benzyl chloroformate in tetrahydrofuran to obtain a compound 2; then, taking the compound 2 to react with diphenyl chlorophosphate and lithium hexamethyldisilazide to obtain a compound 3; inserting carbonyl into the compound 3 in the presence of CO under the action of palladium acetate and triphenylphosphine to obtain a compound 4; under the action of hydrogen and palladium on carbon, carrying out hydrogenation reduction again to obtain a target compound 5. A formula is shown I in the description. The compound prepared by the synthesis method is a useful immediate or product synthesized by a plurality of medicines.

Description

technical field [0001] The invention relates to a synthesis method of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid. Background technique [0002] 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirone-[3,5]nonane-2,7-dicarboxylic acid and related derivatives in medicinal chemistry and Widely used in organic synthesis. At present, there is no literature report on the synthesis of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane-[3,5]nonane-2,7-dicarboxylic acid. There is a certain risk in similar literature reactions, and the route is long and the yield is low. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of 2-tert-butyl-7-methyl-5-oxa-2,8-diazaspirane that has raw material easy to get, easy to operate, easy to control reaction and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10
CPCC07D498/10
Inventor 徐学芹周强于凌波安自强刘月领何燕平焦家盛王瑞琪吴艳徐富军马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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