HCID 53629158, compound → HCID 178439462, compound

HRID 2043616Notes

Reaction equation

HRID 2043616 reaction equation
[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)[C:6](=[O:34])[CH2:5]1)[CH2:2][CH3:3]>CC(O)=O.O>[NH:13]1[CH:14]=[C:10]([CH2:9][N:7]2[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]2=[O:34])[N:11]=[CH:12]1

Participants

3

Reactant 1

HCID 53629158HCID 53629158, compound

Product 1

HCID 178439462HCID 178439462, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

In a 50 ml reaction flask fitted with a magnetic stirrer, 4-propyl-1-[(1-trityl-1H-imidazol-4-yl)methyl]pyrrolidin-2-one x45 (1.8 g, 4 mmol) is dissolved in a 1/1 mixture of CH3CO2H/H2O (30 ml) and the solution is stirred for 36 h at room temperature. Most of the solvents are removed under vacuum and the residue is dissolved in 1N HCl and diluted with CH2Cl2. The first organic phase is removed and pH of the aqueous phase is adjusted to 9 by addition of solid Na2CO3. Then CH2Cl2 is added and the second organic phase is separated, dried over MgSO4 and concentrated to dryness, affording 730 mg of 1-(1H-imidazol-4-ylmethyl)-4-propylpyrrolidin-2-one 110.

Workup

  1. customIn a 50 ml reaction flask
  2. customfitted with a magnetic stirrer
  3. customMost of the solvents are removed under vacuum
  4. dissolutionthe residue is dissolved in 1N HCl
  5. additiondiluted with CH2Cl2
  6. customThe first organic phase is removed
  7. additionpH of the aqueous phase is adjusted to 9 by addition of solid Na2CO3
  8. additionThen CH2Cl2 is added
  9. customthe second organic phase is separated
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-50b67e839a3347fcab29c793845e55ca
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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