反应详情

温度

85 °C

The trans-(3-amino-cyclopentyl)-carbamic acid tert-butyl ester (420 mg, 2.09 mmol) was mixed with 4-fluoro-3-nitrotoluene (342 mg, 2.2 mmol) and potassium carbonate (915 mg, 6.6 mmol) in DMF (20 mL). The stirring mixture was heated at 85° C. for 16.5 hours. The reaction mixture was evaporated under reduced pressure. The residue was partitioned with 50 mL of dichloromethane and 50 mL of brine. The aqueous phase was extracted again with 50 mL of dichloromethane and each organic extract was washed with a portion of brine. After drying, filtering and evaporation of solvents, the crude mixture was purified on silica gel eluting with ethyl acetate and hexanes to give trans-[3-(4-methyl-2-nitro-phenylamino)-cyclopentyl]-carbamic acid tert-butyl ester as a orange oil (305 mg). 1H-NMR is consistent with the assigned structure. LC-MS showed a single peak, C17H25N3O4 (m/e) calcd 335.1845, obsd 336.2 (M+1).

1. customThe reaction mixture was evaporated under reduced pressure
2. customThe residue was partitioned with 50 mL of dichloromethane and 50 mL of brine
3. extractionThe aqueous phase was extracted again with 50 mL of dichloromethane
4. extractioneach organic extract
5. washwas washed with a portion of brine
6. customAfter drying
7. filtrationfiltering
8. customevaporation of solvents
9. customthe crude mixture was purified on silica gel eluting with ethyl acetate and hexanes