[BH4-].[Li+].[CH3:3][O:4][C:5]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:6]=1[CH2:7][N:8]1[C:12](=[O:13])[CH2:11][C:10]([CH3:18])([C:14](OC)=[O:15])[CH2:9]1>C1COCC1.O>[CH3:3][O:4][C:5]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:6]=1[CH2:7][N:8]1[CH2:9][C:10]([CH2:14][OH:15])([CH3:18])[CH2:11][C:12]1=[O:13]Lithium borohydride (28 mg, 1.3 mmol) was added to a solution of methyl 1-(2,4-dimethoxybenzyl)-3-methyl-5-oxopyrrolidine-3-carboxylate (200 mg, 0.65 mmol) in THF (2 mL) at 0° C. The mixture was stirred at room temperature for 16 hours and then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give 1-(2,4-dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one. MS ESI calc'd. for C15H22NO4[M+H]+ 280. found 280. 1H NMR (400 MHz, CD3OD): δ 7.08 (d, J=8.4 Hz, 1H), 6.52 (s, 1H), 6.46 (d, J=8.4 Hz, 1H), 4.40-4.31 (m, 2H), 3.79 (s, 3H), 3.77 (s, 3H), 3.30-3.20 (m, 3H), 2.88-2.86 (m, 1H), 2.43 (d, J=16.8 Hz, 1H), 2.08 (d, J=16.8 Hz, 1H), 1.04 (s, 3H).
Loading…
