Methyl iodide → (+/-)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-methoxy-phenyl)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-hydroxyphenyl)pyrrolidin-2-one (prepared according to the procedure described for Intermediate W, 0.74 g, 2.81 mmol) in acetone (10 mL) was added Cs2CO3 (2.03 g, 5.62 mmol), followed by iodomethane (0.19 mL, 3.1 mmol). The reaction was stirred at room temperature for 72 h and filtered. The filtrate was concentrated under reduced pressure. The resulting oil was purified by flash chromatography (EtOAc) to yield (±)-(4R*,5R*)-5-ethoxycarbonyl-1-methyl-4-(4-methoxy-phenyl)pyrrolidin-2-one (0.72 g, 93%) as a white solid: 1H NMR (DMSO-d6) δ 0.73 (t, J=6.0 Hz, 3H), 2.44-2.71 (m, 5H), 3.56-3.78 (m, 5H), 3.88 (q, J=8.8 Hz, 1H), 4.42 (d, J=8.8 Hz, 1H), 6.82-6.87 (m, 2H), 7.11-7.16 (m, 2H).

Provenance & Evidence