tert-Butanol → HCID 67490940, compound

Participants

Reaction Steps

{(1S,5S,6S)-3-Benzyloxycarbonyl-6-fluoro-3-azabicyclo[3,3,0]octan-1-yl}carboxylic acid tert-butyl ester (354 mg, 0.97 mmol) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (3 mL) was added, and the mixture was stirred for 21 hours. The solvent was evaporated under reduced pressure. A 1N sodium hydroxide solution was added to the resulting residue, and the mixture was washed with chloroform. The aqueous layer was made acidic with a hydrochloric acid solution, followed by extraction with chloroform. The extract was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in toluene (8 mL). Triethylamine (197 mg, 1.95 mmol) and diphenylphosphoryl azide (359 mg, 1.27 mmol) were added in a nitrogen atmosphere, and the mixture was stirred for one hour. Thereafter, tert-butanol (8 mL) was added, and the mixture was stirred at 100° C. for 19 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 136 mg of the title compound as a colorless oil.

Provenance & Evidence