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

HRID 1426893Notes

Reaction equation

HRID 1426893 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1.[CH3:8][C:9]([Si:12](Cl)([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.O>CN(C=O)C>[Si:12]([O:1][C@H:2]1[CH2:6][NH:5][C:4](=[O:7])[CH2:3]1)([C:9]([CH3:11])([CH3:10])[CH3:8])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 185505(R)-(+)-4-Hydroxy-2-pyrrolidinone

Product 1

HCID 149019362-Pyrrolidinone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (4R)-Yield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (R)-4-hydroxypyrrolidin-2-one (purchased from Asta Tech or Aldrich) (5.030 g, 48.26 mmol) in DMF (24 mL) at 0° C. was added TBDMS-Cl (7.637 g, 50.67 mmol) followed by imidazole (4.978 g, 72.39 mmol). The resulting mixture was warmed to ambient temperature and stirred for 1 hour, then poured into 100 mL of water with stirring. The resulting suspension was filtered and the solids were washed with water and dried under reduced pressure to afford (R)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-one (10.14 g, 97.56% yield) that was used directly without further purification.

Workup

  1. stirringwith stirring
  2. filtrationThe resulting suspension was filtered
  3. washthe solids were washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-32b071c3d9484853aff2dc76463cf09d
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

Loading…