Hydrogen Peroxide → HCID 86664657, compound

Participants

Reaction Steps

(1S,5S)-3-Benzyloxycarbonyl-6-methylene-3-azabicyclo[3.2.0]heptane-1-carboxylic acid tert-butyl ester (2.00 g, 5.82 mmol) was dissolved in tetrahydrofuran (40 mL). A 9-borabicyclo[3.3.1]nonane dimmer (0.5 M solution in tetrahydrofuran) (17.5 mL, 8.73 mmol) was added dropwise, and then the mixture was stirred for two hours. A 3 M sodium hydroxide solution (3.49 mL, 10.5 mmol) and 30% aqueous hydrogen peroxide (2.47 mL) were added dropwise to the reaction solution at 0° C., and then the mixture was stirred at room temperature for 16 hours. The reaction solution was extracted with water and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=100:1→1:2) to give 1.58 g of an isomer A (less polar isomer) of the title compound and 50.0 mg of an isomer B (more polar isomer) of the title compound as colorless syrups.

Provenance & Evidence