反应详情

温度

-78 °C

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 aluminumtri-tert-butoxyhydride (1 M in THF, 5481 μl, 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.

1. customwas quenched with 10 mL of 1 N HCl
2. additionthe mixture was diluted with ethyl acetate (500 mL)
3. additionThe reaction was poured into 200 mL of water
4. customthe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
6. washThe combined organics were washed with water, brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated