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

HRID 539013
Notes
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Reaction equation

HRID 539013 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 62649Sodium sulfate decahydrateHCID 67033852(S)-3-(2,4-dimethoxybenzyl)-5-isopropylimidazolidine-2,4-dione

Product 1

HCID 67033222(S)-1-(2,4-dimethoxybenzyl)-4-isopropylimidazolidin-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. temperatureat reflux for 1 hour
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated to a clear oil
  4. customPurification of the crude material by column chromatography
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes