Chlorobenzene → HCID 9832306, compound

Participants

Reaction Steps

Combine 1-(3,4,5-triethoxy-benzoyl)-3-(3,4-dimethoxy-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.31 g, 0.55 mmol), diisopropylethylamine (0.14 g, 1.1 mmol), chlorobenzene (5 mL), and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.28 g, 0.83 mmol) Heat to 120° C. After 4 hours, partition the reaction mixture between ethyl acetate and water. Extract 2 times with water and a 5% sodium bicarbonate solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 3/1 ethyl acetate/hexane and then 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonia to give the title compound: Rf=0.60 (silica gel, 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonia); mp; 155-160° C.

Provenance & Evidence