Ethyl Acetate → HCID 67490840, compound

Participants

Reaction Steps

A 65% solution of Red-Al™ in toluene (1.76 mL, 5.85 mmol) was added dropwise to a solution of (1S,5S)-1-(tert-butoxycarbonylamino)-5-fluoromethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane (707 mg, 1.95 mmol) in toluene in a nitrogen atmosphere at −15° C. over 10 minutes. The mixture was heated to room temperature, stirred for 1.5 hours, and cooled to 0° C. A 25% potassium sodium tartrate tetrahydrate solution (10 mL) was carefully added while maintaining the internal temperature of the reaction solution at 10° C. or less. The reaction solution was poured into a mixture of ethyl acetate (10 mL) and brine (10 mL), followed by extraction with ethyl acetate (150 mL). The organic layer was washed with brine (30 mL) and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→5:1→2:1) to give 567 mg (83%) of the title compound as a pale yellow oil.

Provenance & Evidence