HCID 57857028, compound → HCID 57857042, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution consisting of (3aR,4R,5R,6aS)-4-((E)-3-(benzo[b]thiophen-2-yl)-3-oxoprop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (intermediate 4a prepared in Example 2, Step A) in THF (0.2 M) at −30° C. under a nitrogen atmosphere is slowly added a solution consisting of methylmagnesium bromide in diethyl ether (3 M, 1.5 molar equivalents). The reaction mixture is stirred at −30° C. until the reaction is complete as judged by TLC. Upon completion, the reaction mixture is warmed to 0° C. and is quenched with water and extracted into ethyl acetate. The layers are separated and the aqueous phase is extracted with a fresh portion of ethyl acetate. The organic layers are combined and dried over magnesium sulfate. The solvents are evaporated and the crude material is purified on regular silica gel eluted with an ethyl acetate-hexanes solvent system to afford the title intermediate.

Provenance & Evidence