Methanesulfonic Acid → HCID 68015102, compound

Participants

Reaction Conditions

Reaction Steps

1-[(5-bromo-2-chloro-phenyl)methyl]-4-ethoxy-2,3-difluoro-benzene 3e (5.5 g, 15.3 mmol) was dissolved in 20 mL THF and cooled to −78° C., followed by dropwise addition of a solution of n-BuLi in n-hexane (7.3 mL, 18.3 mmol). The reaction mixture was stirred for 1 hour at −78° C. 30 mL solution of (3R,4S,5R,6R)-3,4,5-tris (trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-one 2f (7.5 g, 16.1 mmol) in THF at −78° C. were added before the reaction mixture was stirred for 2 hours at −78° C. A solution (51 mL) of 0.6 M methanesulfonic acid in methanol was added before the reaction mixture was warmed and stirred for 16 hours at room temperature. Thereafter, the reaction mixture was concentrated under reduced pressure, dissolved in water (50 mL) and extracted with ethyl acetate (100 mL×4). The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 3f (3.05 g, white solid), yield: 45.5%.

Provenance & Evidence