Triphenylphosphine → 2-[[(2R)-4-[(3,4-Dichlorophenyl)methyl]morpholin-2-yl]methyl]isoindoline-1,3-dione

HRID 492118

反応式

HRID 492118 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][NH:6][CH2:7][CH2:8][OH:9].O1C[C@@H]1[CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28].[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:30]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][N:6]1[CH2:30][CH2:29][O:9][C@@H:8]([CH2:17][N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])[CH2:7]1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 2605252-[[(3,4-Dichlorophenyl)methyl]amino]ethanolHCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimideHCID 5363146Diisopropyl azodicarboxylate2 回

生成物 1

HCID 450737512-[[(2R)-4-[(3,4-Dichlorophenyl)methyl]morpholin-2-yl]methyl]isoindoline-1,3-dione収率 69.9%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 2-[(3,4-dichlorobenzyl)amino]ethanol (2.038 g) and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione (2.032 g) in tetrahydrofuran (3.3 ml) was stirred and heated at reflux under nitrogen. After 21.5 h more tetrahydrofuran (12.5 ml) was added and the mixture was cooled to 3°. Triphenyl phosphine (2.793 g) was added and the mixture was stirred until all the solid had dissolved. Diisopropylazodicarboxylate (2.1 ml) was then added over 12 min maintaining the temperature at <7°. After 2.25 h the mixture was allowed to warm to 22°. After 5.3 h more triphenylphosphine (121 mg) and diisopropylazodicarboxylate (0.09 ml) were added. After 22.5 h the reaction mixture was concentrated to near dryness. Propan-2-ol (12 ml) was added and the concentration repeated, this was repeated once more. More propan-2-ol (12 ml) was added and the mixture was heated to 70°. After 0.5 h the slurry was cooled to 22° and then after a further 2 h the product was collected. The bed was washed with propan-2-ol (2×4 ml) and then dried in vacuo at 40° to give the title compound (2.622 g).

後処理

  1. temperatureheated
  2. temperatureat reflux under nitrogen
  3. temperaturethe mixture was cooled to 3°
  4. stirringthe mixture was stirred until all the solid
  5. dissolutionhad dissolved
  6. temperaturemaintaining the temperature at <7°
  7. temperatureto warm to 22°
  8. concentrationAfter 22.5 h the reaction mixture was concentrated
  9. additionPropan-2-ol (12 ml) was added
  10. concentrationthe concentration
  11. additionMore propan-2-ol (12 ml) was added
  12. temperaturethe mixture was heated to 70°
  13. temperatureAfter 0.5 h the slurry was cooled to 22°
  14. customafter a further 2 h the product was collected
  15. washThe bed was washed with propan-2-ol (2×4 ml)
  16. customdried in vacuo at 40°

出典と根拠

ORDレコード
ord-973dec614b7445bbbee6de54322fe380
出典データセット
uspto-grants-2009_05
特許番号
US07531651B2

関連ノート

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