Water → HCID 117997671, compound

Participants

Reaction Steps

To a solution of (1S,2S,3S,5R,6S)-2-((tert-butoxycarbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (D-13-1, 1.30 g) in N,N-dimethylformamide (25 mL), allyl bromide (1.09 mL) and potassium carbonate (1.18 g) were added at room temperature, and the mixture was stirred at the same temperature for 18 hours. To the reaction solution, water was added, and the mixture was extracted three times with ethyl acetate. The combined organic layer was washed three times with 5% saline and once with brine, sequentially. After the organic layer was dried over anhydrous sodium sulfate, the insoluble was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate=100:0-60:40) to give (1S,2S,3S,5R,6S)-diallyl 2-((tert-butoxycarbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylate (D-13-2, 1.49 g) as a colorless oil.

Provenance & Evidence