Cesium carbonate → HCID 68379404, compound

Participants

Reaction Steps

To a solution of 1-bromo-3-nitrobenzene (2.02 g, 0.01 mol) and (S)-2-methylpyrrolidine (1.02 g, 0.012 mol) in 20 mL of 1,4-dioxane was added Cs2CO3 (6.5 g, 0.02 mol) followed by Pd(dba)2 (1.15 g, 0.002 mmol) and X-Phos (476 mg, 0.001 mol) under nitrogen with stirring. The mixture was refluxed for 16 hours under nitrogen. After cooled, the mixture was filtered, and then the filtrate was evaporated by rotary evaporation. The residue was diluted with water and extracted with EtOAc (3×30 mL). The organic layer was washed with brine and dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with (petroleum ether:EtOAc=10:1) to give (S)-2-methyl-1-(3-nitrophenyl)pyrrolidine (1.2 g, 57%) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.47-7.44 (m, 1H), 7.37-7.35 (m, 1H), 7.32-7.27 (m, 1H), 6.86-6.83 (m, 1H), 3.95-3.91 (m, 1H), 3.50-3.44 (m, 1H), 3.26-3.18 (m, 1H), 2.18-1.99 (m, 3H), 1.80-1.72 (m, 1H), 1.21 (d, 2H, J=6.3 Hz). LC-MS: 207 [M+H]+, tR=1.75 min.

Provenance & Evidence