Potassium Carbonate → HCID 86642413, compound

Participants

Reaction Steps

To a solution of (S)-3-aminopyrrolidine-1-carboxylic acid-tert-butyl ester (5 g, 26.88 mmol) and 2-chloro-5-nitropyridine (4.26 g, 26.88 mmol) in THF (100 mL) was added potassium carbonate (7.42 g, 53.76 mmol). The mixture was refluxed for 72 hrs. The mixture was filtered and the filtrate was concentrated. The residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The oily residue was diluted with ether (50 mL) to give a clear solution which was kept at room temperature for 48 hrs. The crystalline material was filtered to give (S)-3-(5-nitro-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid test-butyl ester (6.66 g, 80.5% yield). LCMS for C14H20N4O4 calcd (m/e) 308, obsd 307 (M−H).

Provenance & Evidence