Cesium carbonate → HCID 86700361, compound

Participants

Reaction Steps

A flask was charged with 4-bromo-2-fluoro-1-nitrobenzene (531 mg, 2.41 mmol), Cs2CO3 (2.43 g, 7.46 mmol) and diluted with DMF (6 mL). The reaction mixture was then treated with (S)-tert-butyl 3-aminopyrrolidine-1-carboxylate (0.9 mL, 5.16 mmol) at room temperature and allowed to stir for 16 hours. The mixture was diluted with EtOAc and H2O and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried over Na2SO4, filtered through a small pad of silica gel eluting with 30% EtOAc/Hex, and concentrated in vacuo to afford a crude residue. The flask containing the crude residue was charged with 5 wt % Pt/C (211 mg) and then diluted with 2:1 EtOH/EtOAc (16 mL). The flask was evacuated then backfilled with H2 (3 cycles) and stirred under a hydrogen atmosphere for 20 minutes, at which time, the flask was purged with N2, filtered through a pad of Celite, and concentrated in vacuo to provide a crude residue that was then taken up in AcOH (5 mL). To this was added MeC(OEt)3 (0.5 mL) at room temperature and stirred for 15 minutes, at which time, the solution was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-50% THF/CH2Cl2 gradient) to afford the desired product. LCMS-ESI+: calc'd C17H23BrN3O2: 380.1 (M+H1); Found: 380.1 (M+H+).

Provenance & Evidence