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

HRID 1793790ノート

反応式

HRID 1793790 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc182c6d39aa465a81809ca9d164bfbf
出典データセット
uspto-grants-2006_04
特許番号
US07022677B1

反応ノート

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