Asymmetric synthesis method of chiral benzofuran spirooxindole compound
A technology of benzofuran spiro and oxindole, applied in asymmetric synthesis, organic chemical methods, chemical instruments and methods, etc., can solve the problems of multiple metal wastes and inorganic salts, increased synthesis costs, and poor atom economy. Achieve good reaction characteristics, mild reaction conditions, and simple operation
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0064] Example 1: (2R,3S)-3-(nitromethyl)-2'-oxa-3H-spiro[benzofuran-2,3'-indoline]-1'-tert-butyl ester ;
[0065]
[0066] (A) Take a 10mL clean small test tube, add o-hydroxynitroalkene (0.2mmol, 0.033g), N-Boc protected oxindole (0.2mmol, 0.0932g), organic hydrogen bond catalyst V (0.002mmol, 0.0013g) , solvent acetonitrile (0.5mL), after reacting at 0°C for 24h, a mixture containing intermediate compound 1-A was obtained;
[0067] (B) After removing the solvent from the mixture containing intermediate compound 1-A, add cuprous iodide (0.04mmol, 0.0076g), 85% m-chloroperoxybenzoic acid solid (2mmol, 0.407g), solvent acetonitrile ( 1mL), after reacting at 60°C for 1h, extract with ethyl acetate (3×10mL), desolvate the organic phase under reduced pressure, use ethyl acetate:petroleum ether=1:10 mixed solvent as eluent; 200-300 mesh column Chromatographic silica gel is used as filler, and the target product (0.0341g, 43%yield, 82%ee, >99:1dr) obtained by column chromatogr...
Embodiment 2
[0068] Example 2: (2R,3S)-7-methoxy-3-(nitromethyl)-2'-oxa-3H-spiro[benzofuran-2,3'-indoline]- 1'-tert-butyl ester;
[0069]
[0070] (A) Take 10mL clean small test tube, add 3-methoxy substituted o-hydroxyl nitroalkene (0.2mmol, 0.039g), N-Boc protected oxindole (2mmol, 0.466g), organic hydrogen bond catalyst VI ( 0.04mmol, 0.0101g), solvent tetrahydrofuran (1mL), after reacting at 60°C for 1h, a mixture containing intermediate compound 2-A was obtained;
[0071] (B) After removing the solvent from the mixture containing intermediate compound 2-A, potassium iodide (0.2mmol, 0.076g), 70% aqueous tert-butanol hydroperoxide (2mmol, 0.257g), solvent tetrahydrofuran (1mL) were added, After reacting at 25°C for 6h, extract with ethyl acetate (3×10mL), and desolvate the organic phase under reduced pressure, use ethyl acetate:petroleum ether=1:10 mixed solvent as eluent; 200-300 mesh column chromatography silica gel As filler, the target product (0.0596g, 70%yield, 47%ee, >99:1d...
Embodiment 3
[0072] Example 3: (2R,3S)-7-ethoxy-3-(nitromethyl)-2'-oxa-3H-spiro[benzofuran-2,3'-indoline]- 1'-tert-butyl ester;
[0073]
[0074] (A) Take a 10mL clean small test tube, add 3-ethoxy substituted o-hydroxynitroalkene (0.2mmol, 0.042g), N-Boc protected oxindole (1mmol, 0.233g), organic hydrogen bond catalyst VII ( 0.02mmol, 0.0129g), solvent ethyl acetate (2mL), after reacting at -40°C for 240h, a mixture containing intermediate compound 3-A was obtained;
[0075] (B) After removing the solvent from the mixture containing intermediate compound 3-A, tetrabutylammonium iodide (0.05mmol, 0.0185g), 5% sodium hypochlorite aqueous solution (1mmol, 1.5g), solvent ethyl acetate (4mL ), after reacting for 6h at 25°C, extract with ethyl acetate (3×10mL), and desolvate the organic phase under reduced pressure, use ethyl acetate:petroleum ether=1:10 mixed solvent as eluent; 200-300 mesh column layer Silica gel was used as filler, and the target product (0.0598g, 68%yield, 99%ee, >99:...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
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