Pyrrolidine → 1-[2-Hydroxy-5-(pyrrolidine-1-carbonyl)-phenyl]-ethanone

Participants

Reaction Steps

To a solution of 500 mg (2.8 mmol) of 3-acetyl-4-hydroxy-benzoic acid in 5 mL of DMF, 721.6 μL (4.2 mmol) of TFA-OPfp and 731.5 μL (4.2 mmol) of DIEA were added. The clear solution was stirred at room temperature for 15 minutes, then 467.5 μL (5.6 mmol) of pyrrolidine was added. The mixture was stirred for another hour and was then evaporated to dryness. The oily residue was taken up in 50 mL water-50 mL ethyl acetate mixture, the EtOAc phase was separated, washed twice with 1 M HCl, water, saturated NaHCO3, brine and was dried with Na2SO4. The EtOAc was evaporated; the oil was purified on an open silica gel column using a toluene/ethyl acetate gradient containing 5% acetic acid to yield 410 mg (51%) Compound 18.

Provenance & Evidence