Imidazole → (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

HRID 2080672Notes

Reaction equation

HRID 2080672 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].CN(C)C=O.[OH:19][C@@H:20]1[CH2:24][NH:23][C:22](=[O:25])[CH2:21]1>O>[Si:10]([O:19][C@@H:20]1[CH2:24][NH:23][C:22](=[O:25])[CH2:21]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1550842-Pyrrolidinone, 4-hydroxy-, (4S)-

Product 1

HCID 11074789(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.02 g of imidazole and 1.58 g of t-butyldimethylchlorosilane were added to a dimethylformamide (5 ml) solution of 1.01 g of (S)-4-hydroxy-2-pyrrolidone, and stirred overnight at room temperature. Water was added to the reaction liquid, and stirred with cooling with ice.

Workup

  1. stirringstirred
  2. temperaturewith cooling with ice

Sources & evidence

ORD record
ord-dfda37379d9449df9a9343bbd05bd9f2
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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