tert-Butyl 4-(4-vinyl-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate → tert-Butyl 4-(4-ethyl-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088889Notes

Reaction equation

HRID 2088889 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH:9]=[CH2:10])[N:6]=[C:5]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[H][H]>[Pd].C(O)C>[CH2:9]([C:7]1[N:6]=[C:5]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]2)[N:4]([CH2:3][CH2:2][OH:1])[CH:8]=1)[CH3:10]

Participants

5

Reactant 2

HCID 67112049tert-Butyl 4-(4-vinyl-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67968741tert-Butyl 4-(4-ethyl-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Add 10% palladium on carbon (2.10 g) in ethanol (50 mL). Then add a solution of tert-butyl 4-(1-(2-hydroxyethyl)-4-vinyl-1H-imidazol-2-yl)piperidine-1-carboxylate (20.00 g, 62.22 mmol) in ethanol (200 mL). Cycle through nitrogen and vacuum three times, then hydrogen and vacuum three times. Allow to stir at room temperature under 1 atmosphere hydrogen. After two hours, filter through Celite®. Wash with methanol. Concentrate the filtrate in vacuo to give a light yellow solid as the title compound (20.00 g, 99%). MS (ES) m/z=324 [M]+.

Workup

  1. filtrationfilter through Celite®
  2. washWash with methanol
  3. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-b8bf79b0270f43f3b94f4aae2c50bd4c
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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