Sodium sulfate decahydrate → (S)-1-(2,4-dimethoxybenzyl)-4-isopropylimidazolidin-2-one

HRID 539013Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:10](=O)[C@H:9]([CH:12]([CH3:14])[CH3:13])[NH:8][C:7]1=[O:15].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[CH2:10][C@H:9]([CH:12]([CH3:14])[CH3:13])[NH:8][C:7]1=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-3-(2,4-dimethoxybenzyl)-5-isopropyl-imidazolidine-2,4-dione (0.550 g, 1.88 mmol) in THF (50 mL) at ambient temperature was added bis(2-methoxyethoxy)aluminumhydride (Red-Al) (2.69 ml, 9.41 mmol) and the resultant mixture heated at reflux for 1 hour. The reaction mixture was cooled to 0° C. and sodium sulfate decahydrate was added portion-wise. The resultant thick emulsion was diluted with THF and filtered through a pad of Celite. The filtrate was concentrated to a clear oil. Purification of the crude material by column chromatography, eluting with 1-5% MeOH/dichloromethane, afforded (S)-1-(2,4-dimethoxybenzyl)-4-isopropylimidazolidin-2-one as a colorless solid (0.329 g, 63%). LCMS (APCI+) m/z 279 [M+H]+.

Workup

temperatureat reflux for 1 hour
filtrationfiltered through a pad of Celite
concentrationThe filtrate was concentrated to a clear oil
customPurification of the crude material by column chromatography
washeluting with 1-5% MeOH/dichloromethane

Sources & evidence

ORD record: ord-848de12a89674005a6b62c8b57c45770
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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