Ethanol → HCID 67490849, compound

Participants

Reaction Steps

A 1.09 M solution of a borane/tetrahydrofuran complex in tetrahydrofuran (3.6 mL, 3.98 mmol) was added dropwise to a solution of (1S,5S)-1-(tert-butoxycarbonylamino)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane (548 mg, 1.59 mmol) in tetrahydrofuran (10 mL) at 0° C. over five minutes. After heating to room temperature and stirring for three hours, a 1.09 M solution of a borane/tetrahydrofuran complex in tetrahydrofuran (3.6 mL, 3.98 mmol) was added at the same temperature. The mixture was stirred at room temperature for 15 hours and then cooled to 0° C. A mixture of ethanol (9.0 mL)-water (1.0 mL) was carefully added dropwise. After addition of triethylamine (3.0 mL) dropwise, the mixture was heated to reflux for one hour. The reaction solution was concentrated, and the precipitated white solid was removed by filtration through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→5:1) to give 184 mg (35%) of the title compound as a colorless oil.

Provenance & Evidence