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Preparation method of tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate

A technology of tert-butyl and oxymethylene is applied in the field of preparation of tert-butyl-8-oxyidene-2-azaspiro[4.5]decane-2-carboxylate, which can solve the problem that it is not suitable for amplification, The synthetic route generally has problems such as low yield, which achieves the effect of reasonable reaction process design and saving synthesis cost.

Pending Publication Date: 2020-08-11
SHANGHAI STA PHARMA R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported synthetic routes generally have low yields and are not suitable for scale-up.

Method used

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  • Preparation method of tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate
  • Preparation method of tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate
  • Preparation method of tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Synthesis of 1,4-Dioxaspiro[4.5]decane-8-carbonitrile

[0010]

[0011] Add 500 grams of compound 1 to a 10 L reaction kettle, add 7.5L of ethylene glycol dimethyl ether and 400 mL of ethanol, and then add 812 grams of p-methylsulfonyl methyl isocyanide and 826 grams of tert-butyl in batches at 0°C. Potassium alkoxide. Stir at 0°C for 1 hour and then at 20°C for 3 hours. The reaction solution was slowly poured into 3 L of aqueous solution, extracted three times with 2 L of ethyl acetate, the organic phases were combined, and the organic phase was washed with 2 L of saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column to obtain the product 400 G, the yield is 74.76%.

[0012] Synthesis of 8-(2-chloroethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

[0013]

[0014] 300 mL of a toluene solution of 129 grams of compound 2 was slowly added to 1.2 L of a toluene solution of lithium diisopropylamide at 0 ℃, th...

Embodiment 2

[0023] Synthesis of 1,4-Dioxaspiro[4.5]decane-8-carbonitrile

[0024]

[0025] Add 10 grams of compound 1 and 17 grams of p-methylsulfonyl methyl isocyanide to 10 mL of ethylene glycol dimethyl ether, add 18 grams of potassium tert-butoxide to the reaction solution at 0°C, and stir at 20°C for 12 hours. The reaction solution was poured into saturated ammonium chloride solution, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column to obtain 6.7 g of compound 2 with a yield of 50%.

[0026] Synthesis of 8-(2-chloroethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

[0027]

[0028] Add 60 mL of 6.7 g of compound 2 in tetrahydrofuran at -50 ℃ slowly to 40 mL of lithium diisopropylamide in tetrahydrofuran solution, the reaction solution was stirred at -50 ℃ for 30 minutes, then slowly heated to 20 ℃, stirred for 30 minutes, 6.8 g of 1-bromo-2-chloroethane was added dropwis...

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Abstract

The invention relates to a preparation method of tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate, and mainly aims to solve the technical problems of high raw material cost, difficulty in reaction control, inconvenience in experimental operation and the like in an existing synthesis process. According to the method, tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate is prepared from cheap and easily available 1, 4-dioxaspiro [4.5] decane-8-one as an initial raw material through four steps of reaction. The reaction formula is shown in the specification. The tert-butyl-8-oxo-2-azaspiro-[4.5] decane-2-formate obtained in the invention is a useful intermediate or product synthesized from a plurality of medicines.

Description

Technical field [0001] The invention relates to a method for synthesizing tert-butyl-8-oxylidene-2-azaspiro[4.5]decane-2-carboxylate. Background technique [0002] Tert-butyl-8-oxyylidene-2-azaspiro[4.5]decane-2-carboxylate and related derivatives have important applications in medicinal chemistry and organic synthesis, and have excellent prospects. However, the currently reported synthetic routes generally have low yields and are not suitable for amplification. Therefore, it is of great significance to develop a synthetic method with cheap raw materials readily available, convenient operation, easy batch production control, and suitable overall yield. Summary of the invention [0003] The purpose of the present invention is to develop a kind of tert-butyl-8-oxylidene-2-azaspiro[4.5]decane-2-carboxylate with low raw materials, convenient operation, can be scaled up, and higher yield in four steps. The preparation method. It mainly solves the technical problem that the compound ...

Claims

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Application Information

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IPC IPC(8): C07D209/54
CPCC07D209/54
Inventor 刘月领任文武周强徐学芹张大为徐富军林贺夏成鹏何燕平汪冬冬刘胜攀李梦雪吴艳郝振于凌波马汝建
Owner SHANGHAI STA PHARMA R&D CO LTD
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