Potassium Carbonate → 2,2-Dimethylpropionic acid 2-[(R)-3-(5-fluoro-2-nitrophenylamino)piperidin-1-yl]ethyl ester

Participants

Reaction Steps

To an ice-cooled solution of 2,2-dimethylpropionic acid 2-((R)-3-aminopiperidin-1-yl)ethyl ester (1.675 g, 7.33 mmol) in DMF (30 mL) was added 2,4-difluoronitrobenzene (1.517 g, 9.54 mmol) and potassium carbonate (2.03 g, 14.7 mmol). The reaction mixture was stirred at RT for 16 h, then partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic fractions washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 10-40% EtOAc in cyclohexane) affording the title compound as a yellow oil (2.533 g, 94%). LCMS (Method J): RT 2.31 min [M+H]+ 368.

Provenance & Evidence