Ethyl Acetate → HCID 67490806, compound

Participants

Reaction Conditions

Reaction Steps

A 65% solution of Red-Al™ in toluene (788 mL, 2.63 mol) was added dropwise to a solution of (3S,4S)-3-allyl-4-(tert-butyldimethylsilyloxy)methyl-2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine (327 g, 875 mmol) in toluene (1500 mL) in a nitrogen atmosphere over one hour. The reaction solution was stirred at 45° C. for five hours and then cooled to 0° C., and a 20% (+)-potassium sodium tartrate tetrahydrate solution (2.00 L) was added. The reaction solution was poured into a mixture of ethyl acetate and brine, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1→4:1) to give 213 g of the title compound as a colorless syrup.

Provenance & Evidence