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

Participants

Reaction Conditions

Reaction Steps

A mixture of TMSCI (0.846 mL) and sodium iodide (992 mg) in acetonitrile (12 ml) was added dropwise to a stirred suspension of Intermediate 4 (670 mg) in acetonitrile, cooled to −6° C. and keeping the temperature under 0° C. The RM was stirred at −6° C. and gradually warmed up to room temp overnight. The reaction mixture was partitioned between EtOAc (50 ml) and sat NaHCO3 aq. sol.: water (1:1, 50 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (50 ml). The phases were separated; the organic extracts 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 (94 mg). LC/MS MH+ 389, Rt 1.32 min (2 minute run).

Provenance & Evidence