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

Preparation method of tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2h)-carboxylate

A technology of hydroxyhexahydrofuran and tert-butyl is applied in the field of preparation of tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate, which can solve the problem of lack of suitable problems such as industrial synthesis methods, to achieve the effects of convenient operation, easy reaction and reliable synthesis route

Active Publication Date: 2019-04-30
上海合全医药有限公司
View PDF4 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 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2h)-carboxylate
  • Preparation method of tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2h)-carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: a. Compound 1 (53 g, 0.5 mol) and compound 2 (86 g, 0.5 mol) were dissolved in acetone (300 ml) and heated to 60° C. and stirred overnight. TLC showed that the raw materials disappeared completely. The solution was concentrated under reduced pressure to remove the solvent to obtain compound 3 (132 g) as a yellow solid with a yield of 95%.

[0011] b. Disperse compound 4 (12.5 g, 0.042 mol), palladium on carbon (3 g), triethylamine (6.5 mL, 0.044 mol) and di-tert-butyl carbonate (12 g, 0.046 mol) in ethanol (200 ml) , and then stirred at room temperature under hydrogen (55 psi) pressure for 4 hours. TLC showed complete disappearance of starting material. The reaction solution was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. The crude product was dissolved in ethyl acetate (200ml) and water (150ml). The organic phase was separated, washed twice with saturated brine (200 ml), dried over anhydrous sodium sulfate an...

Embodiment 2

[0022] Example 2: a. Compound 1 (53 g, 0.5 mol) and compound 2 (86 g, 0.5 mol) were dissolved in acetone (300 ml) and heated to 60°C and stirred overnight. TLC showed that the raw materials disappeared completely. The solution was concentrated under reduced pressure to remove the solvent to obtain compound 3 (132 g) as a yellow solid with a yield of 95%.

[0023]b. Disperse compound 4 (125 g, 0.42 mol), palladium on carbon (17 g), triethylamine (65 mL, 0.44 mol) and di-tert-butyl carbonate (115 g, 0.46 mol) in ethanol (1.5 L) , then stirred at room temperature under hydrogen (55 psi) pressure for 4 hours. TLC showed complete disappearance of starting material. The reaction solution was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. The crude product was dissolved in ethyl acetate (500ml) and water (250ml). The organic phase was separated, washed twice with saturated brine (200 ml), dried over anhydrous sodium sulfate and concentra...

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 (3aR, 7S, 7aR)-tertiary butyl 7-hydroxyhexahydrofuro-[3,2-b] pyridine-4(2H)-carboxylic ester, and mainly solves the technical problem of no method suitable for industrial synthesis currently. The preparation method disclosed by the invention comprises nine steps in total; in the ninth step, under the action of sodium borohydride, a pair of compounds 12 and 12A are obtained. ( The structural formulas of the compounds are shown in the description) The compounds obtained by the preparation method are useful intermediates or products synthesized by various medicaments.

Description

technical field [0001] The present invention relates to a preparation method of tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate, namely (3aR,7S,7aR)-tert-butyl 7-hydroxyhexa Synthesis method of hydrofuro[3,2-b]pyridine-4(2H)-carboxylate (MDL: MFCD28122595). Background technique [0002] (3aR,7S,7aR)-tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate and related derivatives are widely used in medicinal chemistry and organic synthesis . At present, there are few reports on the synthesis of (3aR,7S,7aR)-tert-butyl 7-hydroxyhexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate, and there are certain dangers in similar literature reactions Sexuality and route is long, and yield is low. 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 (3...

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 Patents(China)
IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 任文武史桂滨吕秀芝孙宝龙张津铜吴明昆宋艾芳张永丽于凌波马汝建
Owner 上海合全医药有限公司
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