반응 #40679

반응 방정식

O-benzyl-N-(t-butoxycarbonyl)-L-serine

triethylamine

ethyl chloroformate

→

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

수율 89.2%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   여과the reaction mixture was filtered
2. 2
   workup.ADDITIONone piece of ice was added to the filtrate
3. 3
   workup.ADDITIONSodium borohydride (515 mg) was further added
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 6 hrs
5. 5
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
6. 6
   세척after washing with water
7. 7
   건조the organic layer was dried over anhydrous sodium sulfate
8. 8
   기타The solvent was evaporated
9. 9
   기타the obtained crude product
10. 10
    기타was purified by silica gel chromatography (ethyl acetate-hexane)

실험 절차

O-benzyl-N-(t-butoxycarbonyl)-L-serine (2 g) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.22 ml) was added, and ethyl chloroformate (713 μl) was further added dropwise at 0° C. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was filtered, and one piece of ice was added to the filtrate. Sodium borohydride (515 mg) was further added, and the mixture was stirred at room temperature for 6 hrs. The reaction 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 (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (1.7 g)

출처