Toluene → 3-[(4-chlorophenyl)methyl]-2-cyclopropyl-5,6-dihydrocyclopenta[d]imidazol-4(3H)-one

Participants

Reaction Steps

Tetrabutylammonium bromide (270 mg) was added to a stirred mixture of Intermediate 28 (272 mg), 4-chlorobenzyl bromide (414 mg) in sodium hydroxide 20% aq. (3.09 mL) and toluene (10 mL). The RM was stirred at room temp under nitrogen atm. for 16 hours. Sat. NH4Cl aq. solution (50 mL) was added and the mixture was extracted with EtOAc (2×50 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (238 mg). LC/MS MH+ 387, Rt 2.51 min (5 minute run)

Provenance & Evidence