(4-Carboxybutyl)triphenylphosphonium bromide → HCID 57857048, compound

Participants

Reaction Conditions

Reaction Steps

4-Carboxybutyltriphenylphosphonium bromide (55.81 g, 126.0 mmol) was suspended in anhydrous THF (1.5 L) and potassium t-butoxide (252 mL, 252 mmol) was added dropwise at room temperature. After the addition was complete, the orange ylide was cooled to 0° C. and (3aR,4S,5S,6aS)-4-((tert-butyldiphenylsilyloxy)methyl)-5-fluorohexahydro-2H-cyclopenta[b]furan-2-ol (prepared in Step B, 26 g, 63 mmol) as a solution in THF was added dropwise. The reaction mixture was allowed to slowly warm to room temperature overnight with stirring. The reaction was acidified with 5% KHSO4, extracted with ethyl acetate, and washed twice with brine. The crude material was dried over sodium sulfate, filtered and evaporated to an oil. The crude product was purified on silica gel, eluted with hexanes-ethyl acetate (4:1 with 0.4% acetic acid) to afford the title intermediate (30.8 g, 97%).

Provenance & Evidence