Dimethylformamide → tert-Butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088893Notes

Reaction equation

HRID 2088893 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8]OS(C)(=O)=O)[CH:6]=1.CN(C)C=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 67112012tert-Butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Combine tert-butyl 4-(4-bromo-1-(2-(methylsulfonyloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (4.45 g, 9.84 mmol), dimethylformamide (25 mL), and pyrrolidine (2.46 mL, 3.0 eq) under nitrogen. Heat the reaction mixture at 50° C. overnight, then allow to cool to room temperature. Dilute with ethyl acetate. Wash with water followed by saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound (4.12 g, 98%). MS (ES) m/z=427 [M]+.

Workup

  1. temperatureto cool to room temperature
  2. washWash with water
  3. dry with materialDry the organics over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b3617d0d3c8444f2ae099d59c7f54279
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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