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Tert-butyl-7,9-dioxo-2,6-diazaspiro[4.5]decane-2-formate preparation method

A kind of dioxyidene, diazaspiro technology, applied in the preparation of tert-butyl-7,9-dioxidene-2,6-diazaspiro[4.5]decane-2-carboxylate It can solve the problems such as no suitable industrial synthesis method, and achieve the effect of short synthesis route, easy reaction and convenient operation.

Inactive Publication Date: 2019-12-13
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Tert-butyl-7,9-dioxo-2,6-diazaspiro[4.5]decane-2-formate preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: a. Add monoethyl malonate (43 g, 0.324 mol) to a solution of compound 1 (50 g, 0.27 mol) and ammonium acetate (31 g, 0.4 mol) in ethanol (500 mL) at room temperature . Then the reaction solution was heated to reflux and stirred for 18 hours. TLC showed the reaction of the starting material was complete. The reaction was cooled to room temperature and then concentrated under reduced pressure to obtain the crude product. The crude product was diluted with water and adjusted to pH=2-3 with dilute hydrochloric acid aqueous solution, extracted with methyl tert-butyl ether (200 mL) and separated, and the organic phase was discarded. The aqueous phase was basified with sodium carbonate to pH=8-9, then extracted with ethyl acetate (100 mL X 3). The combined organic phases were concentrated under reduced pressure to obtain compound 2 (9 g) as a yellow oil, with a yield of 13%.

[0011] δ = 4.20 - 4.01 (m, 2H), 3.53 - 3.19 (m, 4H), 2.53 (s, 2H), 2.01 -1.76 (m, 4H),...

Embodiment 2

[0016] Example 2: a. Add monoethyl malonate (430 g, 3.24 mol) to a solution of compound 1 (500 g, 2.7 mol) and ammonium acetate (310 g, 4 mol) in ethanol (5 L) at room temperature . Then the reaction solution was heated to reflux and stirred for 18 hours. TLC showed the reaction of the starting material was complete. The reaction was cooled to room temperature and then concentrated under reduced pressure to obtain the crude product. The crude product was diluted with water and adjusted to pH=2-3 with dilute hydrochloric acid aqueous solution, extracted with methyl tert-butyl ether (2 L) and separated, and the organic phase was discarded. The aqueous phase was basified with sodium carbonate to pH=8-9, then extracted with ethyl acetate (1 L X 3). The combined organic phases were concentrated under reduced pressure to obtain compound 2 (89 g) as a yellow oil, with a yield of 13%.

[0017] δ = 4.20 - 4.01 (m, 2H), 3.53 - 3.19 (m, 4H), 2.53 (s, 2H), 2.01 -1.76 (m, 4H), 1.42 (s,...

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Abstract

The invention relates to a tert-butyl-7,9-dioxo-2,6-diazaspiro[4.5]decane-2-formate preparation method. A purpose of the present invention is to mainly solve the technical problem that no method is suitable for industrial synthesis in the prior art. The method comprises four steps, and comprises: dissolving a compound 1 in ethanol to generate a compound 2 under the action of ammonium acetate and monoethyl malonate; in the presence of potassium carbonate, making the compound 2 act with ethyl malonyl chloride in a mixed solution of tetrahydrofuran and water to obtain a compound 3; and carrying out a Dieckmann condensation reaction on the compound 3, toluene and sodium methoxide, treating to obtain a compound 4, and carrying out heating decarboxylating on the compound 4 in water and acetonitrile to obtain a compound 5, wherein the reaction formula is defined in the specification. According to the present invention, the obtained compound can be used as the useful intermediates or productsfor synthesis of a plurality of medicaments.

Description

technical field [0001] The invention relates to a synthesis method of tert-butyl-7,9-dioxylidene-2,6-diazaspiro[4.5]decane-2-carboxylate. Background technique [0002] tert-butyl 7,9-dioxylidene-2,6-diazaspiro[4.5]decane-2-carboxylate and related derivatives are widely used in medicinal chemistry and organic synthesis. There is no report on the synthesis of tert-butyl-7,9-dioxylidene-2,6-diazaspiro[4.5]decane-2-carboxylate. 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 the present invention is to develop a kind of tert-butyl 7,9-dioxylidene-2,6-diazaspiro[4.5]decane which has easy-to-get raw materials, convenient operation, easy-to-control reaction and high yield - Synthetic method of 2-formyl ester. It mainly solves the technical problem that there is no suitable industrial synthesis method at present...

Claims

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Application Information

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IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 史桂滨吕秀芝孙宝龙赵强楚晓丹刘冬靳筱勇崔梦佳于凌波
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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