2-Nitrophenol → Tert-butyl 4-(2-nitrophenoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-nitrophenol (1.5 g, 0.0101 mole) in DMF (15 mL) was added cesium carbonate (16.4 g, 0.0505 mole) followed by 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (3.0 g, 0.0101 mole). The reaction mixture was heated at 80° C. overnight. The mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel 60-120 mesh (20% ethyl acetate in hexane) to afford 1.5 g (47%) of 4-(2-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. LCMS: 323.15 (M+1)+, 98%,

Provenance & Evidence