Sodium Bicarbonate → 1-(3,4,5-Trimethoxy-benzoyl)-3-[2-[4-[1-(4-fluoro-benzyl)-1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(3,4-dimethoxy-phenyl)-pyrrolidine

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Reaction Steps

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.69 g, 1.32 mmol) and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.49 g, 1.42 mmol), and sodium bicarbonate (0.223 g, 2.64 mmol) in tetrahydrofuran/water (15/4) (30 mL). Heat to reflux. After 72 hours, cool and evaporate in vacuo to obtain a residue. Partition the residue between dichloromethane and 5% sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5/1 ethyl acetate/methanol to give an oil. Combine the oil with dichloromethane and extract with 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Dry the residue in vacuo at 82° C. to give the title compound: Rf=0.27 (silica gel, 5/1 ethyl acetate/methanol); mp; 80-83° C. Elemental Analysis calculated for C44H49FN4O7: C 69.09; H 6.46; N 7.32; Found: C 68.82; H 6.44; N 7.42.

Provenance & Evidence