Preparation method of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane [3,5] nonane-7-carboxylic ester

A technology of azaspirone and iodomethyl, applied in the preparation of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane[3,5]nonane-7-carboxylate field, it can solve the problems of no suitable industrial synthesis method, and achieve the effect of convenient operation, easy reaction and short route

Inactive Publication Date: 2016-03-30
上海药明康德新药开发有限公司 +2
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  • Abstract
  • Description
  • Claims
  • 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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  • Preparation method of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane [3,5] nonane-7-carboxylic ester
  • Preparation method of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane [3,5] nonane-7-carboxylic ester

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Experimental program
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Effect test

Embodiment 1

[0010] Embodiment 1: a, compound 1 (50g, 0.25mol) and zinc powder (49.2g, 0.75mol) were suspended in a mixed solution of tetrahydrofuran and aqueous ammonium chloride (2 / 3, 500mL). Control the temperature at -10-10°C, add the compound dropwise to the reaction solution 2 (109.3 g, 0.90 mol). The temperature of the reaction is slowly raised to 15-40° C., and the reaction is continued for 2-5 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. Ethyl acetate (100mLx3) was used for the reaction solution. The organic phases were combined, dried with sodium sulfate, filtered and concentrated by vacuum distillation to obtain a crude product. The crude product was purified by silica gel column (petroleum ether / ethyl acetate volume ratio=30 / 1 to 10 / 1) to obtain a colorless oily compound 3 (60 g), yield 99.9%.

[0011] δ(CDCl 3 )=5.827-5.740,1H),5.151-5.067(m,2H),3.776-3.739(m,2H),3.137-3.061(m,2H),2.176-2.157(d, J =7.6,2H), 1.593-1....

Embodiment 2

[0014] Embodiment 2: a, compound 1 (500g, 2.5mol) and zinc powder (492g, 7.5mol) were suspended in a mixed solution of tetrahydrofuran and ammonium chloride aqueous solution (2 / 3, 5L). Control the temperature at -10-10°C, add the compound dropwise to the reaction solution 2 (1.1kg, 9.0mol). The temperature of the reaction is slowly raised to 15-40° C., and the reaction is continued for 2-5 hours. TLC (petroleum ether / ethyl acetate volume ratio=2 / 1) showed that the reaction was complete. Ethyl acetate (1Lx3) was used for the reaction solution. The organic phases were combined, dried with sodium sulfate, filtered and concentrated by vacuum distillation to obtain a crude product. The crude product was purified by silica gel column (petroleum ether / ethyl acetate volume ratio=30 / 1 to 10 / 1) to obtain a colorless oily compound 3 (600g), yield 99.9%.

[0015] δ(CDCl 3 )=5.827-5.740,1H),5.151-5.067(m,2H),3.776-3.739(m,2H),3.137-3.061(m,2H),2.176-2.157(d, J =7.6,2H), 1.593-1.485...

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Abstract

The invention relates to a preparation method of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane [3,5] nonane-7-carboxylic ester and mainly solves the technical problem that no appropriate industrial synthesis method exists at present. The method comprises two steps as follows: firstly, a compound 1 and a compound 2 produce a compound 3 under the action of zinc powder and ammonium chloride, then the compound 3 reacts with iodine and sodium bicarbonate in acetonitrile, a compound 4 is obtained, and the equation is shown in the specification. The compound obtained with the method is a useful intermediate for synthesis of numerous drugs or product.

Description

technical field [0001] The invention relates to a synthesis method of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane[3,5]nonane-7-carboxylate (CAS: 1160246-84-3). Background technique [0002] tert-butyl 2-iodomethyl-1-oxa-7-azaspirane[3,5]nonane-7-carboxylate and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few syntheses about tert-butyl 2-iodomethyl-1-oxa-7-azaspirane[3,5]nonane-7-carboxylate, and similar literature reactions have certain dangers and routes long and the yield is low. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of this invention is to develop a kind of tert-butyl 2-iodomethyl-1-oxa-7-azaspirane [3,5] that has raw materials that are easy to get, easy to operate, easy to control and high in yield. Synthetic method of nonane-7...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107
CPCC07D491/107
Inventor 于凌波史桂滨李甜甜孙宝龙金星崔梦佳刘冬吕秀芝吴明坤庞洲宋艾芳徐博任文武马汝建尚慕宏
Owner 上海药明康德新药开发有限公司
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