2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester → 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester

HRID 2101500Notes

Reaction equation

HRID 2101500 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)[CH3:2]>C(O)C.[Ni].O>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:6][C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[CH:9]=[CH:10][N:11]=1)[CH3:2]

Participants

5

Reactant 1

HCID 688632652-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester

Product 1

HCID 119553452-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl esterYield 94%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester, (409 mg, 0.99 mmol) in absolute ethanol (30 mL) was added Raney nickel active catalyst (approximately 1 g of a 50% suspension in water). The reaction flask was flushed with N2 prior to flushing with H2 via a balloon. The reaction was stirred at ambient temperature for 14 h under a balloon atmosphere of H2. After flushing with N2, the reaction was filtered through a plug of celite and the filtrate concentrated in vacuo. The resulting residue was partitioned with CH2Cl2 (10 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to afford 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-propionic acid ethyl ester (385 mg, 94%) as a colorless oil: ESI MS m/z 417 [C22H22Cl2N2O2+H]+.

Workup

  1. customThe reaction flask was flushed with N2
  2. customto flushing with H2 via a balloon
  3. customAfter flushing with N2
  4. filtrationthe reaction was filtered through a plug of celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting residue was partitioned with CH2Cl2 (10 mL) and saturated NaHCO3 (5 mL)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f841fe2ba5724e2ba0e30990a5541df5
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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