Hydrochloric Acid → tert-Butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088886Notes

Reaction equation

HRID 2088886 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:5]([CH2:7][CH2:8][O:9]C2CCCCO2)[CH:6]=1.O1CCCC1.Cl>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67265112tert-Butyl 4-(4-bromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 67265139tert-Butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine tert-butyl 4-(4-bromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (5.00 g, 10.91 mmol), tetrahydrofuran (150 mL), and 1 M aqueous hydrochloric acid (50 mL); let stir overnight at room temperature. Dilute with ethyl acetate. Wash with excess 1M aqueous sodium hydroxide, followed by saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a yellow foam (3.84 g, 94%). MS (ES) m/z=376 [M]+.

Workup

  1. washWash with excess 1M aqueous sodium hydroxide
  2. dry with materialDry the organics over anhydrous magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e4e2d84b9462414580b2e8027db94071
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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