반응 #1126845

반응 방정식

(S)-3-(tert-butoxycarbonyl)-4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate

lithium aluminum tri-tert-butoxyhydride

→

(2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate

수율 99.6%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   기타was quenched with 10 mL of 1 N HCl
2. 2
   workup.ADDITIONthe mixture was diluted with ethyl acetate (500 mL)
3. 3
   workup.ADDITIONThe reaction was poured into 200 mL of water
4. 4
   기타the layers were separated
5. 5
   추출the aqueous layer was extracted with ethyl acetate (3×100 mL)
6. 6
   세척The combined organics were washed with water, brine
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

A solution of (S)-3-(tert-butoxycarbonyl)-4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate (1100 mg, 2741 μmol) in 45 mL of ethanol cooled to 0° C. was added to lithium aluminum tri-tert-butoxyhydride (1 M in THF, 5481 μA 5481 μmol) in 15 mL of ethanol at −78° C. dropwise via cannula over 5 minutes. After stirring at −78° C. for 2 hours the reaction was quenched with 10 mL of 1 N HCl and the mixture was diluted with ethyl acetate (500 mL). The reaction was poured into 200 mL of water, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organics were washed with water, brine, and dried over sodium sulfate, filtered and concentrated to provide (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate (1060 mg, 96% yield) as a white solid.

출처