4-(Trifluoromethyl)aniline → Methyl 3-(4-trifluoromethylanilino)pentanoylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-trifluoromethylaniline (121 mg, 0.75 mmol) and methyl 2-pentenoylcarbamate (79 mg, 0.5 mmol) in toluene (2 ml) in a stream of nitrogen was added Pd((R)-binap)(H2O)2(OTf)2 (13.3 mg, 0.0125 mmol) and the resulting mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the reaction mixture was concentrated and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to give the objective compound methyl 3-(4-trifluoromethylanilino)pentanoylcarbamate (143 mg, 45% yield). Enantiomeric excess ratio of this product was determined by a liquid chromatography using a column for separation of optical isomers (column: OJ-R) to be 59% e.e. (S form).

Provenance & Evidence