반응 #40680

반응 방정식

lithium chloride

potassium carbonate

m-cresol

t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate

methanesulfonyl chloride

→

t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate

용매

dimethylformamide

dichloromethane

dimethylformamide

ethyl acetate

dichloromethane

triethylamine

반응 조건

후처리

1. 1
   세척after washing with water
2. 2
   건조the organic layer was dried over anhydrous sodium sulfate
3. 3
   기타The solvent was evaporated
4. 4
   기타to give a crude product
5. 5
   workup.STIRRINGthe mixture was stirred overnight at 40° C
6. 6
   기타The solvent was evaporated
7. 7
   workup.ADDITIONthe residue was diluted with ethyl acetate
8. 8
   세척washed with water
9. 9
   건조The organic layer was dried over anhydrous sodium sulfate
10. 10
    기타the solvent was evaporated
11. 11
    기타to give a crude product
12. 12
    workup.STIRRINGthe mixture was stirred overnight at 90° C
13. 13
    세척after washing with water
14. 14
    건조the organic layer was dried over anhydrous sodium sulfate
15. 15
    기타The solvent was evaporated
16. 16
    기타the obtained crude product
17. 17
    기타was purified by silica gel chromatography (ethyl acetate-hexane)

실험 절차

To t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (3.23 g) obtained in Step 1 were added dichloromethane (40 ml), methanesulfonyl chloride (1.07 ml) and triethylamine (3.20 ml), and the mixture was stirred at 0° C. for 3 hrs. The reaction mixture was diluted with dichloromethane and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated to give a crude product. To this crude product were added dimethylformamide (30 ml) and lithium chloride (2.4 g), and the mixture was stirred overnight at 40° C. The solvent was evaporated, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated to give a crude product. To this crude product were added dimethylformamide (20 ml), potassium carbonate (2.4 g) and m-cresol (1.47 ml), and the mixture was stirred overnight at 90° C. The mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate (1.5 g).

출처