Acetic Acid → {(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

7.71 g of sodium hydride (content: 60%) (193 mmol) was added portionwise to a solution of 30.92 g of (+)-2,3-O-isopropylidene-L-threitol (191 mmol) in N,N-dimethylformamide (285 ml) under a nitrogen atmosphere and under ice-cooling over 45 minutes, and the mixture was stirred at the same temperature for one hour. 23.8 ml of benzyl bromide (200 mmol) was added to the reaction mixture over 30 minutes, and the mixture was stirred at the same temperature for three hours. 2.2 ml of acetic acid (38 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=2/1-1/1) to obtain 35.27 g of the title compound (yield: 73%).

1. temperaturecooling over 45 minutes
2. stirringthe mixture was stirred at the same temperature for three hours
3. stirringthe mixture was further stirred at room temperature for one hour
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additiondiluted with water
6. extractionfollowed by extraction with ethyl acetate
7. washThen, the organic layer was washed with water and brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationAfter filtration
10. customthe solvent was evaporated under reduced pressure
11. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=2/1-1/1)

ORD record

ord-e3dae4a1e2b14237903721fb940d30e1

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158790B2