Cesium carbonate → HCID 57857026, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution consisting of (Z)-7-((1R,2S,3S,5S)-2-((tert-butyldiphenylsilyloxy)methyl)-3-fluoro-5-hydroxycyclopentyl)hept-5-enoic acid (prepared in Step C, 30.8 g, 61.6 mmol) in anhydrous DMF (1.2 L) was added cesium carbonate (30.0 g, 92.4 mmol) followed by iodopropane (22 g, 13 mL, 130 mmol). The reaction mixture was heated to 50° C. and stirred for 1.5 hours, monitoring by TLC. The reaction mixture was acidified with 5% KHSO4, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified on silica gel, eluted with hexanes-ethyl acetate (4:1) to afford the title intermediate (28.6 g, 86%).

Provenance & Evidence