Imidazole → methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpropanoate

HRID 1917289Notes

Reaction equation

HRID 1917289 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:14][O:15][C:16](=[O:21])[C@H:17]([CH3:20])[CH2:18][OH:19].O>CN(C)C=O>[CH3:14][O:15][C:16](=[O:21])[C@H:17]([CH3:20])[CH2:18][O:19][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 5324733Roche ester (R)

Product 1

HCID 11831316methyl (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpropanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (6.44 g, 42.8 mmol) and tert-butyldimethylsilyl chloride (6.05 g, 88.8 mmol) were added to a solution of (R)-3-hydroxy-2-methylpropionic acid methyl ester (5.0 g, 42.33 mmol) in dimethylformamide (50 mL), and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, followed by extraction with hexane twice. The extract was then dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 9.3 g (95%) of the title compound as a colorless oil.

Workup

  1. extractionfollowed by extraction with hexane twice
  2. dry with materialThe extract was then dried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc4b0235125c4c108b5210a959731c9b
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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