تفاعل #40680

معادلة التفاعل

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

المذيبات

dimethylformamide

dichloromethane

dimethylformamide

ethyl acetate

dichloromethane

triethylamine

ظروف التفاعل

المعالجة

1. 1
   غسيلafter washing with water
2. 2
   تجفيفthe organic layer was dried over anhydrous sodium sulfate
3. 3
   أخرىThe solvent was evaporated
4. 4
   أخرىto give a crude product
5. 5
   workup.STIRRINGthe mixture was stirred overnight at 40° C
6. 6
   أخرىThe solvent was evaporated
7. 7
   workup.ADDITIONthe residue was diluted with ethyl acetate
8. 8
   غسيلwashed with water
9. 9
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
10. 10
    أخرىthe solvent was evaporated
11. 11
    أخرىto give a crude product
12. 12
    workup.STIRRINGthe mixture was stirred overnight at 90° C
13. 13
    غسيلafter washing with water
14. 14
    تجفيفthe organic layer was dried over anhydrous sodium sulfate
15. 15
    أخرىThe solvent was evaporated
16. 16
    أخرىthe obtained crude product
17. 17
    أخرىwas purified by silica gel chromatography (ethyl acetate-hexane)

الإجراء التجريبي

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).

المصدر