Imidazole → (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

HRID 2080683Notes

Reaction equation

HRID 2080683 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].CN(C)C=O.[OH:19][C@H:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25]>O>[Si:6]([O:19][C@H:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11029774(3S)-3-hydroxypyrrolidin-2-one

Product 1

HCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-oneYield 42.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an ice bath, 570 mg of imidazole and 947 mg of t-butyldimethylsilyl chloride were added to a dimethylformamide (5 ml) solution of 503 mg of (3S)-3-hydroxypyrrolidin-2-one, and stirred at room temperature for 1 hour. Water was added to the reaction liquid, extracted with ethyl acetate, the organic layer was washed with water and saturated saline water, and dried. The solvent was evaporated away under reduced pressure to obtain 452 mg of the entitled compound as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated saline water
  3. customdried
  4. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-87688e58680947d8998560456a7d42a5
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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