Ethanol → HCID 67490881, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, to a solution of (1R,5R)-1-(tert-butoxycarbonylamino)-5-chloro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane (217 mg, 0.573 mmol) in THF (10 mL) was added 1.0M borane-THF complex in THF solution (1.72 mL, 1.72 mmol) at room temperature. After stirring for 14 hours, 1.0M borane-THF complex in THF solution (0.86 mL, 0.86 mmol) was added. The mixture was warmed to 50° C., and stirred for 18 hours. To the mixture was further added 1.0M borane-THF complex in THF solution (0.86 mL, 0.86 mmol) and the mixture was stirred for 24 hours at 50° C. After being cooled to 0° C., to the mixture were added water (1 mL), EtOH (9 mL) and triethylamine (1 mL). The mixture was warmed to 80° C., and stirred for 2 hours. The solvent was distilled off under reduced pressure. To the residue were added saturated aqueous solution of ammonium chloride and ethyl acetate. The separated organic layer was washed with water and brine. The solution was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel flush column chromatography (10% ethyl acetate/hexane) to afford 67.3 mg of the title compound as a colorless oil.

Provenance & Evidence