Diisopropylethylamine → HCID 131736795, compound

Participants

Reaction Steps

To a solution of triphosgene (35 mg) in chloroform (4 mL), 4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one (45.9 mg) and a solution of N,N-diisopropylethylamine (0.18 mL) in tetrahydrofuran (4 mL) were added at room temperature. After the mixture was stirred at the same temperature for 30 minutes, a solution of (1S,2S,3S,5R,6S)-diallyl 2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylate (D-13-3, 100 mg) in chloroform (4 mL) was added to the reaction mixture, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate was added, and the organic layer was washed once with water 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=90:10-70:30) to give (1S,2S,3S,5R,6S)-diallyl 3-fluoro-2-((((5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy)carbonyl)amino)bicyclo[3.1.0]hexane-2,6-dicarboxylate (D-15-1, 60.0 mg) as a colorless amorphous.

Provenance & Evidence