Triethylamine → (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

6-Chloro-3-nitropyridin-2-amine (1.25 g, 7.22 mmol) was added to a solution of (R)-ethyl piperidine-3-carboxylate (2.0 g, 10.32 mmol) and triethylamine (2.87 mL, 20.65 mmol) in acetonitrile (25 mL) at room temperature. The reaction mixture was stirred for 3 h at 80° C., then was cooled and was partitioned between ethyl acetate and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 0-25% ethyl acetate in petroleum ether) to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (2 g). MS (ES+APCI) (M+H) 295.0; LCMS retention time 5.246 min (Method R1).

Provenance & Evidence