Ethyl Acetate → Ethyl [3-[(4-chlorophenyl)methyl]-4-hydroxy-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl acetate (1.08 mL) in 2-methylTHF (1 ml) was added dropwise to a stirred solution of LiHMDS, 1M in THF (11.1 mL) cooled to −78° C. under nitrogen atm. The mixture was stirred at −78° C. under nitrogen for 30 mins. Then Intermediate 3 (700 mg) in 2-methylTHF (5 ml) was added dropwise. The RM was stirred at −78° C. under nitrogen for 4 hours. An excess of sat NH4Cl aq. sol. was added and the resulting suspension was warmed up to room temp and extracted with EtOAc (100 ml). The phases were separated and the aqueous layer was again extracted with EtOAc (50 ml), the phases were separated. The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica (100 g) using a dichloromethane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (670 mg) LC/MS MH+ 405, Rt 0.89 min (2 minute run).

Provenance & Evidence