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Preparation method of 4-methyl formate-2-oxo-1,8-diazaspiro[4.5]decane-8-tert-Butyl formate

A technology for tert-butyl formate and diazaspiro, which is applied in the field of preparation of 4-methyl formate-2-oxo-1,8-diazaspiro[4.5]decane-8-tert-butyl formate, To achieve the effect of reasonable reaction process design and saving synthesis cost

Inactive Publication Date: 2019-04-19
武汉药明康德新药开发有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, there is currently no complete synthetic route report

Method used

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  • Preparation method of 4-methyl formate-2-oxo-1,8-diazaspiro[4.5]decane-8-tert-Butyl formate

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[0011] Step 1: Dissolve compound 1 (100 g, 434.29 mol) in dimethyl sulfoxide (500 mL) and stir at 25 °C, then add tetrabutylammonium iodide (160.41 g, 434.29 mmol) and potassium fluoride ( 126.15 g, 2.17 mol). After 10 minutes, dimethyl maleate (312.96 g, 2.17 mol, 272.14 mL,) was added and the temperature was raised to 40°C for 22 hours. TLC (petroleum ether / ethyl acetate volume ratio = 3 / 1) showed that the reaction was complete. Water (2.5 L) was added to the reaction system, and then extracted with tert-butyl dimethyl ether (500 mL x 5). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by a silica gel column ( Gradient elution: petroleum ether / ethyl acetate ~ petroleum ether / ethyl acetate volume ratio = 5:1 ~ 10:1) to obtain yellow oily compound 2 (140.2 g, 374.48 mmol) with a yield of 86%.

[0012] 1 CHLOROFORM-d, 400 MHz

[0013] δ 4.17 - 3.97 (m, 2H), 3.79 (s, 1H), 3.74 (s...

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Abstract

The invention relates to a preparation method of 4-methyl formate-2-oxo-1,8-diazaspiro[4.5]decane-8-tert-Butyl formate and mainly solves the technical problem that there is no method suitable for industrial synthesis so far. The preparation method comprises the following two steps: Step 1, a compound 1 and dimethyl maleate react under the action of tetrabutylammonium iodide and potassium fluoridewith dimethyl sulfoxide used as a solvent to generate a compound 2; and Step 2, the compound 2 is subjected to raney nickel / H2 catalytic hydrogenation in methanol used as a solvent to obtain a compound 3, namely 4-methyl formate-2-oxo-1,8-diazaspiro[4.5]decane-8-tert-Butyl formate. The reaction equation is as shown in the specification.

Description

technical field [0001] The invention relates to a preparation method of methyl 4-formate-2-oxo-1,8-diazaspiro[4.5]decane-8-formate tert-butyl. Background technique [0002] tert-butyl 4-methylcarboxylate-2-oxo-1,8-diazaspiro[4.5]decane-8-carboxylate (PubChem ID: 545357) and related derivatives are important in medicinal chemistry and organic synthesis application, has excellent prospects. However, there is no complete synthetic route report so far. Therefore, it is of great significance to develop a synthetic method that is easy to obtain cheap raw materials, easy to operate, easy to control the reaction in batch production, and suitable for the overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of raw material cheap, easy to operate, can enlarge, two-step higher yield synthesis 4-formic acid methyl ester-2-oxo-1,8-diazaspiro[4.5]decane-8 -The preparation method of tert-butyl formate. The method mainly solves the...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 张大为周强白有银高明飞付新雨姚宝元谭汝鹏孔祥南刘鲜赵廷王曦孙春卢荣昌刘雨雷魏昕睿于凌波马汝建
Owner 武汉药明康德新药开发有限公司
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