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Synthesis method of 8-(tertbutyloxycarbonyl)-1-oxa-8-azacyclospiro [4.5] decane-2-carboxylic acid

A technology of tert-butoxycarbonyl and synthetic method, applied in the synthesis field of 8-(tert-butoxycarbonyl)-1-oxa-8-azaspiro[4.5]decane-2-carboxylic acid, can solve the problem of no It is suitable for problems such as industrial synthesis methods, and achieves the effects of reasonable reaction process design, easy reaction and short route.

Inactive Publication Date: 2017-10-27
SHANGHAI SYNTHEALL PHARM CO LTD +4
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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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  • Synthesis method of 8-(tertbutyloxycarbonyl)-1-oxa-8-azacyclospiro [4.5] decane-2-carboxylic acid

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Embodiment 1

[0012] The compound magnesium chips (143 g, 5.97 mol) was dissolved in anhydrous tetrahydrofuran (2000 mL), then compound 1 (400 g, 2.98 mol) dissolved in anhydrous tetrahydrofuran (2000 mL) was added at room temperature, and then refluxed for 1 hour , the reaction system was not treated, and the crude compound 2 (206.7 g) was obtained and used directly in the next step. Mixture 2 (2.98 mol) was slowly added dropwise to compound 2A (457 g, 2.30 mol) dissolved in 2000 ml at 0°C. Then the reaction solution was stirred at 12°C for 14 hours. TLC (petroleum ether / ethyl acetate volume ratio = 5 / 1) showed that the reaction was complete. It was then quenched with 2 L of aqueous ammonium chloride at 0 °C. Then the system was filtered; the filtrate was extracted three times with 600*3 ml of ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (gradient elution: petroleum...

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Abstract

The invention relates to a synthesis method of 8-(tertbutyloxycarbonyl)-1-oxa-8-azacyclospiro [4.5] decane-2-carboxylic acid, and mainly solves the technical problem that a synthesis method suitable for industrialization does not exist in the prior art. The synthesis method comprises four steps that 1, firstly, a compound of 4-bromine-1-butene and magnesium chips are subjected to backflow reaction in a solvent of anhydrous tetrahydrofuran to prepare a corresponding Grignard reagent compound 2; 2, the compound 2 and N-tertbutyloxycarbonyl-4-piperidone react at room temperature to prepare a compound 3; 3, the compound 3 and metachloroperbenzoic acid react in a solvent of methylene dichloride to prepare a compound 4; 4, the compound 4 is oxidized in a methylene dichloride solution to obtain a final compound 5. The reaction formulas are shown in the specification.

Description

technical field [0001] The invention relates to a synthesis method of compound 8-(tert-butoxycarbonyl)-1-oxa-8-azaspiro[4.5]decane-2-carboxylic acid. Background technique [0002] Compound 8-(tert-butoxycarbonyl)-1-oxa-8-azaspiro[4.5]decane-2-carboxylic acid (CAS: 1160246-88-7) and related derivatives in medicinal chemistry and organic synthesis has wide application. At present, there are few reports on the synthesis methods of 8-(tert-butoxycarbonyl)-1-oxa-8-azaspiro[4.5]decane-2-carboxylic acid. 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, and a higher yield of 8-(tert-butoxycarbonyl)-1-oxa-8-azaspiro[4.5]decane- 2-Carboxylic acid synthesi...

Claims

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Application Information

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IPC IPC(8): C07D491/107
CPCC07D491/107
Inventor 王志全汪永生张宏伟毛晶庞州王密于淼代攀攀杨云龙于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD