4-Nitrophenol → 1-(2-(4-Nitrophenoxy)ethyl)pyrrolidine

Participants

Reaction Steps

To a mixture of PPh3 (866 mg, 3.3 mmol) in THF (6 mL) is added DIAD (0.65 mL, 3.3 mmol) at 0° C. The suspension was stirred for 10 minutes, then heated to room temperature. To the mixture, 4-nitrophenol (460 mg, 3.3 mmol) and 1-(2-hydroxyethyl)-pyrrolidine (0.26 mL, 2.2 mmol) is added, and the mixture is stirred at room temperature for 16 hours, then concentrated. The residue is taken up in EtOAc, washed with 1N NaOH aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=1:99 to 10:90) to give 277 mg of 1-[2-(4-Nitro-phenoxy)-ethyl]-pyrrolidine as a white solid.

Provenance & Evidence