Imidazole → 1-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(((tert-butyl(dimethyl)silyl)oxy)methyl)pyrrolidin-2-one

HRID 632769Notes

Reaction equation

HRID 632769 reaction equation
[Br:1][C:2]1[C:3]([N:8]2[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][C:9]2=[O:15])=[N:4][N:5]([CH3:7])[CH:6]=1.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27])[CH2:10][C:9]2=[O:15])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1180616531-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 1317354531-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(((tert-butyl(dimethyl)silyl)oxy)methyl)pyrrolidin-2-oneYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(hydroxymethyl)pyrrolidin-2-one (84 mg) and 1H-imidazole (27 mg) in DMF (3.0 mL) was added tert-butyldimethylchlorosilane (54 mg). The reaction mixture was stirred at room temperature for 20 hr, and diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (44 mg).

Workup

  1. washThe diluted solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bbaedd97d20349169f01334457e394e8
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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