Iodoethane → 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-2-ethyl-butyric acid methyl ester

Temperature

-78 °C

To a solution of (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid methyl ester (70 mg, 0.12 mmol) in dry THF (50 mL) was added lithium diisopropylamide (1.7 mL, 1.2 mmol) dropwise with cooling to −78° C. After the reaction mixture was stirred at −78° C. for an additional 1 h, iodoethane (0.4 mL) was added. The reaction was warmed to RT over 4 h followed by quenching with saturated ammonium chloride (10 mL). Solvent was removed and the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (37 mg, 50%). MS m/e 652.2 (M+H)+.

1. temperatureThe reaction was warmed to RT over 4 h
2. customby quenching with saturated ammonium chloride (10 mL)
3. customSolvent was removed
4. customthe residue was partitioned between water and ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80)

ORD record

ord-37a7da44aee145abb17a538293705978

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560586B2