3-(Trifluoromethyl)aniline → HCID 90311569, compound

Participants

Reaction Steps

A mixture of 3-(benzyloxy)-5-methylcyclopent-2-enone (intermediate 22, 210 mg, 1.04 mmol) and Palladium on carbon (10%, 127 mg) in toluene (3.0 mL) is treated with hydrogen (3.4 bar) for 9 h. The mixture is filtered, and the filtrate is treated with 3-(tri-fluormethyl)aniline (130 μL, 1.04 mmol) and Ytterbium(III) trifluormethanesulfonate (3 mg, 5 μmol) and stirred at room temperature over night. Another portion of 3-(trifluor-methyl)aniline (65 μL, 0.52 mmol) is added, and the mixture is stirred over night. Water and dichloromethane is added, and the phases are separated. The organic phase is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 136 mg; ESI mass spectrum [M+H]+=256; Retention time HPLC: 0.55 min (X012_S01).

Provenance & Evidence