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Preparation method of 1-benzyl-8-tert-butyl-2-(hydroxymethyl)-diazaspirane decane dicarboxylate

A technology of azaspirone and dicarboxylate, which is applied in the field of preparation of 1-benzyl 8-tert-butyl 2--diazaspiroane decane dicarboxylate, can solve the problem that there is no suitable industrial synthesis method and other problems, to achieve the effect of short synthetic route, easy reaction and convenient operation

Inactive Publication Date: 2017-11-24
SHANGHAI SYNTHEALL PHARM CO LTD +4
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  • Abstract
  • Description
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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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  • Preparation method of 1-benzyl-8-tert-butyl-2-(hydroxymethyl)-diazaspirane decane dicarboxylate

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Embodiment 1

[0010] Example 1: a. Compound 1 (3 g, 18 mmol) was dissolved in anhydrous dichloromethane (30 mL), the reaction solution was lowered to 0°C, oxalyl chloride (3 mL) was added dropwise thereto, and then N , N-dimethylformamide (0.03 mL), after the dropwise addition, the reaction was carried out at room temperature for 5 hours. The mixture was distilled under reduced pressure to obtain crude compound 2 (3 g) as a brown oil, with a yield of 100%.

[0011] b. Dissolve compound 2 (3 g, 18 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.3 g, 23 mmol) in dichloromethane (40 mL), and cool the reaction system to 0°C, Therein, triethylamine (4.5 g, 45 mmol) was slowly added dropwise, and the reaction was controlled at zero to continue the reaction for 4 hours. TLC (petroleum ether / ethyl acetate volume ratio=3 / 1) showed that the reaction was complete. The reaction solution was washed twice with water and saturated brine respectively, dried over sodium sulfate, filtered and concentr...

Embodiment 2

[0016] Example 2: a. Compound 1 (300 g, 1.8 mol) was dissolved in anhydrous dichloromethane (2 L), the reaction solution was lowered to 0°C, oxalyl chloride (300 mL) was added dropwise thereto, and then N,N-Dimethylformamide (3 mL), after the dropwise addition, the reaction was carried out at room temperature for 5 hours. The mixture was distilled under reduced pressure to obtain compound 2 (332 g) as a brown oil, with a yield of 100%.

[0017] b. Dissolve compound 2 (332 g, 1.8 mol) and N,O-dimethylhydroxylamine hydrochloride (228 g, 2.3 mol) in dichloromethane (4 L), cool the reaction system to 0°C, Therein, triethylamine (454.5 g, 4.5 mol) was slowly added dropwise, and the reaction was controlled at zero to continue the reaction for 4 hours. TLC (petroleum ether / ethyl acetate volume ratio=3 / 1) showed that the reaction was complete. The reaction solution was washed twice with water and saturated brine respectively, dried over sodium sulfate, filtered and concentrated by d...

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Abstract

The invention relates to a preparation method of 1-benzyl-8-tert-butyl-2-hydroxymethyl-1,8-diazaspirane[4.5]decane-1,8-dicarboxylate, mainly aiming at solving the technical problem that a suitable industrial synthesis method does not exist at present. The preparation method comprises six steps: firstly, taking a compound 1 and oxalyl chloride to react in dichloromethane, so as to generate a compound 2; then obtaining a compound 3 under the action of triethylamine; then taking the compound 3 to react with a vinyl Grignard reagent, so as to obtain a compound 4; then taking the compound 4 and a compound 5 to react under the condition that DBU is used as alkali, so as to obtain a compound 6; carrying out hydrogenation ring closure to obtain a compound 7; finally, taking the compound 7 to react with benzyl chloroformate under an alkaline condition, so as to obtain a final product 8. The compound prepared by the preparation method is used as a useful intermediate or product for synthesizing various medicines.

Description

technical field [0001] The present invention relates to the preparation method of 1-benzyl 8-tert-butyl 2-(hydroxymethyl)-diazaspiroane decane dicarboxylate, i.e. 1-benzyl 8-tert-butyl 2-hydroxymethyl - Preparation method of 1,8-diazaspiro[4.5]decane-1,8-dicarboxylate (CAS: 1445951-83-6). Background technique [0002] 1-Benzyl 8-tert-butyl 2-hydroxymethyl-1,8-diazaspiro[4.5]decane-1,8-dicarboxylate and related derivatives in medicinal chemistry and organic synthesis Has a wide range of applications. At present, there are few reports on the synthesis of 1-benzyl 8-tert-butyl 2-hydroxymethyl-1,8-diazaspiro[4.5]decane-1,8-dicarboxylate, and similar literature reactions exist Certain danger and route are long, and 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 this invention is to develop a k...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 任文武史桂滨吕秀芝孙宝龙张津铜吴明昆宋艾芳张永丽于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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