3-Nitroaniline → HCID 90052103, compound

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)-3-pyrrolidinone (220 mg) and 3-nitroaniline (164 mg) in methylene chloride (3 mL), sodium triacetoxyborohydride (375 mg) and acetic acid (67 μL) were added at room temperature, and the mixture was stirred at the same temperature for 10 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 50% hexane in ethyl acetate) to obtain tert-butyl 3-((3-nitrophenyl)amino)pyrrolidine-1-carboxylate (C23, 210 mg).

Provenance & Evidence