HCID 131726527, compound → HCID 11183982, compound

HRID 1295821Notes

Reaction equation

HRID 1295821 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:12]([CH2:13][N:14]2[CH2:18][CH:17]([CH2:19][CH2:20][CH3:21])[CH2:16][C:15]2=[O:22])[CH:11]=[N:10][CH:9]=1)(C)(C)C>CC(O)=O.C1COCC1.O>[OH:6][CH2:7][C:8]1[N:12]([CH2:13][N:14]2[CH2:18][CH:17]([CH2:19][CH2:20][CH3:21])[CH2:16][C:15]2=[O:22])[CH:11]=[N:10][CH:9]=1

Participants

3

Reactant 1

HCID 131726527HCID 131726527, compound

Product 1

HCID 11183982HCID 11183982, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

In a 250 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, 1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-ylmethyl]-4-propyl-pyrrolidin-2-one a30 (0.5 g, 0.0014 mol) is heated at 80° C. in a AcOH/THF/H2O mixture (9 ml/3 ml/3 ml) for 9 h, then stirred overnight at room temperature and concentrated in vacuo. The residue is dry by azeotropic distillation with toluene, purified by chromatography on silicagel (CH2Cl2/MeOH) and the solid is recrystallized from AcOEt to give 1-{[5-(hydroxymethyl)-1H-imidazol-1-yl]methyl}-4-propylpyrrolidin-2-one 80 (0. 1 14 g, 35%).

Workup

  1. concentrationconcentrated in vacuo
  2. dry with materialThe residue is dry by azeotropic distillation with toluene
  3. custompurified by chromatography on silicagel (CH2Cl2/MeOH)
  4. customthe solid is recrystallized from AcOEt

Sources & evidence

ORD record
ord-8574573e44f94adba1b4f2418e2a552a
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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