[1-(4-Methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid → HCID 57719045, compound

HRID 1985179Notes

Reaction equation

HRID 1985179 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11](=O)[CH:10]([CH2:13][C:14](O)=[O:15])[N:9]([CH2:17][CH2:18][CH3:19])[C:8]2=[O:20])=[CH:4][CH:3]=1>C1COCC1>[OH:15][CH2:14][CH2:13][CH:10]1[CH2:11][N:7]([CH2:6][C:5]2[CH:21]=[CH:22][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:8](=[O:20])[N:9]1[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 1

HCID 57719268[1-(4-Methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid

Product 1

HCID 57719045HCID 57719045, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [1-(4-methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid (3.23 g, 10.6 mmol) in THF (50 mL) is treated dropwise with 1 M solution of borane-THF complex in THF (53.1 mL, 53.1 mmol) and then stirred at room temperature under N2 for 4 hours. The reaction is quenched with methanol (30 mL) and stirred at room temperature for 16 hour. The solvent is removed to give crude product that is purified by flash chromatography using 97.5/2.5 CH2Cl2:MeOH to afford 2.46 g (84%) 4-(2-hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one. 1H NMR. MS (ES+) Calc'd for C16H25N2O2 (M+1) 277. Found m/z 277 (100%).

Workup

  1. customThe reaction is quenched with methanol (30 mL)
  2. stirringstirred at room temperature for 16 hour
  3. customThe solvent is removed
  4. customto give crude product that
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-9bcf91a50da344f2bceb3fb71744fc17
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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