Lithium borohydride → 1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-4-methylpyrrolidin-2-one
Reaction equation
[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]Participants
Procedure
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).
Workup
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-4827b0486b2845f788b74e9b26859fd3
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242984B2
Reaction notes
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