Ethanol → HCID 67490841, compound

Participants

Reaction Steps

{(1S,5R,6S)-6-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3,3,0]octan-1-yl}carboxylic acid tert-butyl ester (402 mg, 1.16 mmol) was dissolved in tetrahydrofuran (20 mL), and a 1 M borane-tetrahydrofuran complex (5.79 mL, 5.79 mmol) was added dropwise in a nitrogen atmosphere. After two hours, a 1 M borane-tetrahydrofuran complex (3.47 mL, 3.47 mmol) was added; after 14 hours, a 1 M borane-tetrahydrofuran complex (3.47 mL, 3.47 mmol) was further added. After stirring for 2.5 hours, ethanol (18 mL), water (2 mL), and triethylamine (2 mL) were added, and the mixture was stirred at 80° C. for two hours. The reaction solution was evaporated under reduced pressure, and a saturated ammonium chloride solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in dichloromethane (2.8 mL). Benzyloxycarbonyl chloride (1.03 g, 6.04 mmol) was added, and the mixture was stirred at 40° C. for 14 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (25% ethyl acetate/hexane) to give 359 mg of the title compound as a colorless oil.

Provenance & Evidence