Phthalimide → (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

HRID 1793790Notes

Reaction equation

HRID 1793790 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4]O.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CCO)CC>C1COCC1>[O:3]1[CH2:1][C@H:2]1[CH2:4][N:10]1[C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]2[C:6]1=[O:16]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 7497DiethylethanolamineHCID 11776TriphenylphosphineHCID 5460455(+)-Glycidol

Product 1

HCID 719415(R)-(-)-N-(2,3-Epoxypropyl)phthalimideYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To THF solution (400 ml) of (R)-(+)-glycidol 2.47 g (32 mmol), phthalimide 7 g (47.6 mmol), triphenyl phosphine 14.3 g (54.5 mmol) and molecular shieve 4 Å 30 g were added at room temperature and then DEAE 8.7 g (50 mmol) was added dropwise under cooling on ice-bath. The reaction mixture was allowed to stand at room temperature overnight. Molecular shieve was removed by filtration and filtrate was evaporated to dryness in vacuo. The desired product was further purified by silica gel chromatography. 4.9 g of desired product was obtained as an oil. The NMR spectra were consistent with the desired title intermediate.

Workup

  1. temperatureunder cooling on ice-bath
  2. customMolecular shieve was removed by filtration and filtrate
  3. customwas evaporated to dryness in vacuo
  4. customThe desired product was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-bc182c6d39aa465a81809ca9d164bfbf
Source dataset
uspto-grants-2006_04
Patent number
US07022677B1

Reaction notes

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