tert-butyl 4-(1-(1-(benzyloxycarbonyl)piperidin-3-yl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate → tert-butyl 4-(2-oxo-5-phenyl-1-(piperidin-3-yl)-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate

HRID 1685122Notes

Reaction equation

HRID 1685122 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:20]([C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)=[O:29])[NH:19][C:18]2=[O:43])[CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[O:43]=[C:18]1[NH:19][C:20]([C:28]([N:30]2[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]2)=[O:29])=[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]1[CH:13]1[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 24999588tert-butyl 4-(1-(1-(benzyloxycarbonyl)piperidin-3-yl)-2-oxo-5-phenyl-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate

Product 1

HCID 59292653tert-butyl 4-(2-oxo-5-phenyl-1-(piperidin-3-yl)-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 mL of methanol was added to a flask containing 16F (0.50 g, 0.85 mmol) prepared in the previous step and 10% Pd/C (0.05 g). The reaction flask was evacuated and purged with hydrogen, then stirred under a balloon of hydrogen overnight at RT. The mixture was filtered over a pad of Celite and the filtrate was concentrated in vacuo. The residue was reconstituted in ethyl acetate, washed with brine, dried over MgSO4, and concentrated to give tert-butyl 4-(2-oxo-5-phenyl-1-(piperidin-3-yl)-2,3-dihydro-1H-imidazole-4-carbonyl)piperazine-1-carboxylate (16H), as a glassy oil in quantitative yield. ESI-MS: m/z 456.4 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. custompurged with hydrogen
  3. filtrationThe mixture was filtered over a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f720b605a829450bad5e14de6759d701
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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