3-(3-Benzyloxypropyl)imidazolidine-2,4-dione → 3-(3-Hydroxypropyl)imidazolidine-2,4-dione

HRID 2068104Notes

Reaction equation

HRID 2068104 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][NH:14][C:13]1=[O:18])C1C=CC=CC=1>CO>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][NH:14][C:13]1=[O:18]

Participants

3

Reactant 1

HCID 670192263-(3-Benzyloxypropyl)imidazolidine-2,4-dione

Product 1

HCID 433936853-(3-Hydroxypropyl)imidazolidine-2,4-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-Benzyloxypropyl)imidazolidine-2,4-dione (1.3 g, 5.26 mmol) was dissolved in methanol (15 ml) and the system purged with nitrogen. 10% Palladium on carbon (130 mg, 10% by mass) and a few drops of glacial acetic acid were added and the mixture stirred under a hydrogen atmosphere (1 atmosphere) for 3 days. The mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (98/2 to 95/5) to give 3-(3-hydroxypropyl)imidazolidine-2,4-dione (606 mg, 73%) as a viscous oil which crystallised on standing.

Workup

  1. customthe system purged with nitrogen
  2. addition10% Palladium on carbon (130 mg, 10% by mass) and a few drops of glacial acetic acid were added
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (98/2 to 95/5)

Sources & evidence

ORD record
ord-13213b873ee44ca1b57a337fdc077e67
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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