Ethyl Acetate → HCID 67490866, compound

Participants

Reaction Steps

A 65% solution of Red-Al™ in toluene (1.43 mL, 4.75 mmol) was added dropwise to a solution of (1S,5S)-1-(tert-butoxycarbonylamino)-5-methoxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane (593 mg, 1.58 mmol) in toluene in a nitrogen atmosphere at 0° C. over two minutes. The mixture was heated to room temperature, stirred for two hours, and cooled to 0° C. A 20% 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 (100 mL). The organic layer was washed with brine (20 mL), and then dried over anhydrous sodium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→9:1) to give 244 mg (43%) of the title compound as colorless crystals.

Provenance & Evidence