Ethyl Acetate → HCID 69351806, compound

Participants

Reaction Steps

5% carbon-palladium (1.I g) was added to an ethyl acetate (50 ml) solution of tert-butyl(1R)-(-)-1-[3-(5-chloro-2-nitrophenoxy)phenyl]ethylcarbamate (3.5 g, 8.9 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure for 1 hour. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure. The residue was stirred with ethyl 4-bromobutyrate (7 g, 36 mmols), potassium carbonate (3.7 g, 27 mmols) and N,N-dimethylformamide (50 ml) at 80° C. for 72 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[N-[2-[3-[(1R)-1-tert-butoxycarbonylaminoethyl]phenoxy]-4-chlorophenyl]]aminobutyrate (2.4 g, 56%).

Provenance & Evidence