Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF0 Cites 0 Cited by
  • Summary
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Examples

Experimental program
Comparison scheme
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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com