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

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).

1. customunder 0° C
2. temperaturegradually warmed up to room temp overnight
3. customThe reaction mixture was partitioned between EtOAc (50 ml)
4. customThe two phases were separated
5. extractionthe aqueous phase was extracted again with EtOAc (50 ml)
6. customThe phases were separated
7. customdried (hydrophobic frit)
8. concentrationconcentrated under vacuum
9. customThe residue was purified on silica using a cyclohexane
10. concentrationconcentrated under vacuum

ORD record

ord-d859b6bc59544d00b548c88f8427b569

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399444B2