Water → (S)-4-Isopropylimidazolidin-2-one

HRID 2401264Notes

Reaction equation

HRID 2401264 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([C@@H:10]1[NH:14][C:13](=[O:15])[NH:12][C:11]1=O)[CH3:9].O.[OH-].[Na+]>C(OCC)C.C(O)C.C1COCC1>[CH3:7][CH:8]([C@H:10]1[CH2:11][NH:12][C:13](=[O:15])[NH:14]1)[CH3:9]

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 853633AC1LgxvoHCID 21226445Aluminium lithium hydride

Product 1

HCID 24808374(S)-4-Isopropylimidazolidin-2-oneYield 32.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (290 mg) in diethyl ether (20 mL) was added (5S)-5-(propan-2-yl)imidazolidine-2,4-dione (540 mg) while cooling in ice, and the mixture was stirred at room temperature overnight. After cooling in ice, water (1 mL), 4M aqueous sodium hydroxide solution (1 mL), THF (15 mL) and ethanol (2 mL) were added thereto, and the resulting mixture was stirred at room temperature for 10 min. After filtration through Celite (registered trademark), the filtrate was concentrated under reduced pressure to afford (4S)-4-(propan-2-yl)imidazolidin-2-one (160 mg).

Workup

  1. temperaturewhile cooling in ice
  2. temperatureAfter cooling in ice
  3. stirringthe resulting mixture was stirred at room temperature for 10 min
  4. filtrationAfter filtration through Celite (registered trademark)
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0f901b1a0fb4c018c91ba77d1b9eaeb
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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