Potassium Carbonate → 1-(3,4,5-Trimethoxy-benzoyl)-3-[2-[4-[1-(4-fluoro-benzyl)-1 H-benzoimidazol-2-yl]-4-hydroxy-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

Participants

Reaction Conditions

Reaction Steps

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.70 g, 1.3 mmol) and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazol-2-yl]-4-hydroxy-piperidine (0.58 g, 1.8 mmol), and potassium carbonate (0.37 g, 2.7 mmol) in dimethylformamide (22 mL). Heat to 70-75° C. After 4 days, cool and evaporate in vacuo to obtain a residue. Partition the residue between ethyl acetate and water. Extract the organic layer with water and a saturated solution of potassium carbonate. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 2/1 ethyl acetate/methanol to give a foam. Combine the foam with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain the title compound: Rf=0.37 (silica gel, 2/1 ethyl acetate/methanol); mp; 110-120° C.

Provenance & Evidence