Diethyl Malonate → HCID 118101242, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl 2-bromo-5-nitrobenzyl(methyl)carbamate (3.000 g, 7.91 mmol), copper(i) iodide (0.301 g, 1.582 mmol), L-proline (0.364 g, 3.16 mmol) and cesium carbonate (5.16 g, 15.82 mmol) were mixed in a pressure vial and degassed (3×). A solution of diethyl malonate (1.501 mL, 9.89 mmol) in DMSO (10 mL) was added, the reaction mixture was degassed again and stirred at 50° C. for 3 days. The cooled reaction mixture was partitioned between EtOAc (100 mL) and NH4Cl (aq. std.; 100 mL). The organic layer was washed with brine (2×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-40% EtOAc/hexane). Fractions were combined and concentrated under reduced pressure to give 15A (2.668 g, 5.82 mmol, 73.6% yield) as a colorless syrup. MS (ESI) m/z: 459.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 8.18 (1H, d, J=8.53 Hz), 8.09 (1H, br. s.), 7.72 (1H, d, J=7.28 Hz), 7.36 (5H, d, J=15.81 Hz), 5.20 (3H, br. s.), 4.67 (2H, br. s.), 4.07-4.28 (4H, m), 2.81 (3H, s), 1.24 (6H, t, J=7.15 Hz).

Provenance & Evidence