Imidazole → 2-Pyrrolidinone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4R)-

HRID 385838Notes

Reaction equation

HRID 385838 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1.N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>CN(C=O)C>[Si:13]([O:1][C@H:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1528074-Hydroxy-2-pyrrolidinone

Product 1

HCID 149019362-Pyrrolidinone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4R)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-2-pyrrolidone (1.00 g, 9.89 mmol) was suspended in DMF (25 mL) and cooled to 0° C. Imidazole (1.01 g, 14.84 mmol) and TBS—Cl (1.57 g, 10.39 mmol) were added and the reaction was then warmed to room temperature. After 30 minutes the reaction was poured into water (˜50 mL) and the resulting white precipitate was collected by filtration, dried in an oven, and used without further purification.

Workup

  1. temperaturethe reaction was then warmed to room temperature
  2. filtrationthe resulting white precipitate was collected by filtration
  3. customdried in an oven
  4. customused without further purification

Sources & evidence

ORD record
ord-cbef15278a9a4577852f9ef33c15e709
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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