Preparation method of tert-butyl-1-oxo-6-oxa-9-azaspiro[4.5]decane-9-carboxylate

A technology of oxyethylene and tert-butyl, applied in the field of preparation of tert-butyl-1-oxyethylene-6-oxa-9-azaspiro[4.5]decane-9-carboxylate, It can solve the problems of no suitable industrial synthesis method and achieve the effects of reasonable reaction process design, strong repeatability and easy reaction

Inactive Publication Date: 2019-04-12
SHANGHAI STA PHARMA R&D CO LTD
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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 tert-butyl-1-oxo-6-oxa-9-azaspiro[4.5]decane-9-carboxylate

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Embodiment 1

[0012] Compound 1 (50 g, 204 mmol) was dissolved in 600 mL of tetrahydrofuran, cooled to -78 degrees Celsius, and under nitrogen protection, lithium hexamethyldisilazide (1M, 0.255L) was added dropwise to the reaction system. Stir for one hour under nitrogen protection at -78°C, and add bromentene (37 g, 0.25 mol) and 100 mL of tetrahydrofuran dropwise into the reaction system at -78°C. After the dropwise addition was complete, the reaction was raised to 20° C. and stirred for 12 hours. After the reaction, the reaction solution was poured into 400 mL of ammonium chloride aqueous solution, extracted three times with ethyl acetate, dried and spin-dried to obtain 30 g of the crude product of compound 2 as a yellow oil, yield: 47%.

[0013] To a mixed solvent of compound 2 (30 g, 96 mmol), sodium periodate (82 g, 383 mmol) in 150 ml of water and 150 mL of acetone, potassium permanganate (9.84 g, 623 mmol) was added in batches at 0°C. After the dropwise addition was completed, the...

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Abstract

The invention relates to a preparation method of tert-butyl-1-oxo-6-oxa-9-azaspiro[4.5]decane-9-carboxylate, and mainly solves the technical problem that no suitable industrial synthesis method existsat present. The preparation method comprises the following five steps: step 1, dissolving a compound 1 in tetrahydrofuran, dropwise adding lithium hexamethyldisilazide under protection of nitrogen, then adding bromopentene, and after the reaction is finished, treating the obtained crude product compound 2; step 2, adding potassium permanganate into a mixed solvent of the compound 2, sodium periodate and acetone in batches, and carrying out treatment after a reaction is completed to obtain a compound 3; step 3, dissolving the compound 3 and cesium carbonate in acetonitrile, dropwise adding iodomethane, and carrying out treatment after a reaction is completed to obtain a compound 4; step 4, sequentially adding the compound 4 and potassium tert-butoxide into tetrahydrofuran, and carrying outtreatment after a reaction is completed to obtain a compound 5; and step 5, adding the compound 5 into hydrochloric acid, adjusting alkalinity after a reaction is completed, then adding Boc anhydride, carrying out stirring for a reaction, and carrying out treatment to obtain a compound 6.

Description

technical field [0001] The invention relates to a method for preparing compound tert-butyl-1-oxyethylene-6-oxa-9-azaspiro[4.5]decane-9-carboxylate. Background technique [0002] Compound tert-butyl-1-oxyylidene-6-oxa-9-azaspiro[4.5]decane-9-carboxylate (CAS: 1251000-29-9) and related derivatives in Medicinal Chemistry It has wide applications in organic synthesis. At present, there is no literature report on the synthesis method of 4-tert-butyl 2-methylmorpholine-2,4-dicarboxylate. 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 tert-butyl-1-oxoylidene-6-oxa-9-azaspiro[4.5]decane that has raw materials that are easy to get, easy to operate, and easy to control the reaction. -The synthetic method of 9-formyl ester. It mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/34
CPCC07D265/34
Inventor 李红周强任文武何米娜蒋欣欣吴东平李庆攀何华敬安自强刘月领吴艳何燕平焦家盛于凌波马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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