反应详情

温度

80 °C

[RuCl(p-cymene)((R)-segphos)]Cl(17.6 mg, 0.0192 mmol), methyl 3-oxopentanoate (500 mg, 3.842 mmol), 4-trifluoromethylaniline (619 mg, 3.842 mmol) and 2-propanol (2.5 mL) were placed in a 2.5 mL-stainless autoclave under atmosphere of nitrogen, and the mixture was stirred under a hydrogen pressure of 3 MPa at 80° C. for 15 hours. After completion of the reaction, the solvent was removed by evaporation in vacuo, and the residue was purified by column chromatography on silica gel (eluent: hexane ethyl acetate=3/1) to give methyl (3R)-3-(4-trifluoromethylphenylamino)-pentanoate (109 mg) as a colorless oil in 10.3% yield. The enantiomeric excess of the product was found to be 92.7% ee determined by HPLC analysis using a SUMICHIRAL OA-2500 column (available from SUMIKA CHEMICAL ANALYSIS SERVICE LTD.).

1. customAfter completion of the reaction
2. customthe solvent was removed by evaporation in vacuo
3. customthe residue was purified by column chromatography on silica gel (eluent: hexane ethyl acetate=3/1)