Tetrabutylammonium Fluoride Trihydrate → HCID 57425267, compound

HRID 1642762Notes

Reaction equation

HRID 1642762 reaction equation
Br[CH2:2][CH2:3][C@H:4]([NH:10][O:11][Si](C(C)(C)C)(C)C)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-]>C1COCC1>[O:11]1[CH2:2][CH2:3][C@@H:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:10]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 58017533HCID 58017533, compound

Product 1

HCID 57425267HCID 57425267, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2S)-4-bromo-2-({[tert-butyl(dimethyl)silyl]oxy}amino)butanoate (870 mg, 2.556 mmol) in THF (25 mL) was added tetrabutylammoniumfluoride trihydrate (887 mg, 2.812 mmol) and the mixture was stirred at rt for 1 h. The solvents were evaporated and the residue was purified by flash chromatography (DCM/EtOAc 9:1, then 4:1) to give ethyl (3S)-isoxazolidine-3-carboxylate (340 mg, 91%) as an oil.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by flash chromatography (DCM/EtOAc 9:1

Sources & evidence

ORD record
ord-3a931e70e251455b9d1bb9fe802b0672
Source dataset
uspto-grants-2012_02
Patent number
US08119673B2

Reaction notes

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