Ethyl Acetate → HCID 57857073, compound

Participants

Reaction Conditions

Reaction Steps

(3aR,4R,5R,6aS)-4-(3,3-Difluoro-4-phenoxybutyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one, prepared in Step E, was dissolved in anhydrous THF (0.5 M) under nitrogen atmosphere and cooled to −78° C. A solution consisting of DIBAL-H (2 molar equivalents, 1 M in toluene) is added to the reaction mixture dropwise and stirred for 3 hours. Ethyl acetate (20 mL) is added and the mixture is stirred for an additional 5 minutes. The mixture is subsequently treated with 30% aqueous K, Na tartrate and stirred vigorously overnight. The layers are separated and the organic phase is filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes to afford the title intermediate.

Provenance & Evidence