Phthalimide → 2-((2R)-2-phenylpropyl)isoindoline-1,3-dione

HRID 392934ノート

反応式

HRID 392934 の反応式
[C:1]1([C@@H:7]([CH3:10])[CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[C:1]1([C@@H:7]([CH3:10])[CH2:8][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 177050(+)-2-Phenyl-1-propanolHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 213073412-((2R)-2-phenylpropyl)isoindoline-1,3-dione収率 112.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

An oven dried 250.0 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel with a continuous nitrogen blanket is charged with (2R)-2-phenylpropan-1-ol (2.0 mL, 14.32 mmol), phthalimide (2.1 g, 14.32 mmol), triphenylphosphine (5.63 g, 21.48 mmol) and THF (70.0 mL). To this solution at room temperature was then added a solution of diethylazodicarboxylate (3.38 mL, 21.48 mmol) dissolved in THF (10.0 mL) over a period of 15-20 minutes (reaction exothermed slightly to 50° C. by the end of addition went from clear to reddish color). Stirred reaction to room temperature overnight). To the red solution was added water (50.0 mL) and the organic extracted with chloroform (140.0 mL). Dried the organic solution with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to an oil. To the oil was added heptane (150.0 mL) with stirring. Filtered of precipitates, then concentrated filtrate to an oil. Plug filtration of the oil over silica gel with 1:1 ethylacetate/hexane and concentrating product fractions afforded the intermediate title compound, 2((2R)-2-phenylpropyl)isoindoline-1,3-dione, (4.27 g, 96%) as an oil which solidified on equilibrating to room temperature; 1H nmr (CDCl3, 300 MHz) δ 1.3 (d, 3H), 3.3-4.0 (m, 1H), 3.7-3.9 (m, 2H), 7.1-7.3 (aromat. m, 2H), 7.63-7.7 (aromat. m, 2H), 7.8-7.85 (aromat. m, 4H).

後処理

  1. dry with materialAn oven dried 250.0 mL three necked round bottom flask
  2. customequipped with a mechanical stirrer
  3. additionthermometer, addition funnel with a continuous nitrogen blanket
  4. customreaction exothermed slightly to 50° C.
  5. additionby the end of addition
  6. customreaction to room temperature overnight)
  7. extractionthe organic extracted with chloroform (140.0 mL)
  8. dry with materialDried the organic solution with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure to an oil
  11. additionTo the oil was added heptane (150.0 mL)
  12. stirringwith stirring
  13. filtrationFiltered
  14. customof precipitates
  15. filtrationPlug filtration of the oil over silica gel with 1:1 ethylacetate/hexane
  16. concentrationconcentrating product fractions

出典と根拠

ORDレコード
ord-6b7c7862200f45cb831e7670afac6668
出典データセット
uspto-grants-2004_10
特許番号
US06803484B2

反応ノート

読み込み中…