反应 #1880972

ord-bc182c6d39aa465a81809ca9d164bfbf

反应方程式

CCN(CC)CCO
DEAE
OC[C@@H]1CO1
(R)-(+)-glycidol
O=C1NC(=O)c2ccccc21
phthalimide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
O=C1c2ccccc2C(=O)N1C[C@@H]1CO1
desired product
收率 75.4%
O=C1c2ccccc2C(=O)N1C[C@@H]1CO1
N-(2(R), 3-Epoxypropyl)phthalimide
收率 75.4%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度under cooling on ice-bath
  2. 2
    其他Molecular shieve was removed by filtration and filtrate
  3. 3
    其他was evaporated to dryness in vacuo
  4. 4
    其他The desired product was further purified by silica gel chromatography

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07022677B1uspto-grants-2006_04