Aluminium lithium tri-tert-butoxide hydride → (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate

Temperatur

-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 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.

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

ORD-Eintrag

ord-06810a685fa14a8aae50ce052be6348b

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08552181B2