2,2-Dipropyloxirane → 2-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

HRID 1189957ノート

反応式

HRID 1189957 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH2:22]([C:25]1([CH2:28][CH2:29][CH3:30])[CH2:27][O:26]1)[CH2:23][CH3:24]>CCO.O>[OH:26][C:25]([CH2:28][CH2:29][CH3:30])([CH2:22][CH2:23][CH3:24])[CH2:27][NH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 134110112,2-DipropyloxiraneHCID 221249642-(3-(3-Aminophenyl)propyl)isoindoline-1,3-dione

生成物 1

HCID 672991752-(3-(3-(2-Hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

To a stirred solution of 2-(3-(3-aminophenyl)propyl)isoindoline-1,3-dione (0.50 g, 1.78 mmol) in EtOH:H2O (9:1), 2,2-dipropyloxirane (0.45 g, 3.57 mmol) was added and the reaction mixture was stirred under reflux for 36 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (20% to 30% EtOAc—hexanes gradient) gave 2-(3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propyl)isoindoline-1,3-dione as a yellow semisolid. Yield (0.22 g, 30%); 1H NMR (400 MHz, DMSO-d6) δ 7.86-7.81 (m, 4H), 6.92 (t, J=7.8 Hz, 1H), 6.45 (s, 1H), 6.41 (d, J=8.0 Hz, 1H), 6.37 (d, J=7.6 Hz, 1H), 4.89 (bs, 1H), 4.16 (s, 1H), 3.59 (t, J=7.2 Hz, 2H), 2.87 (d, J=5.2, 2H), 2.46-2.50 (m, 2H), 1.83-1.90 (quintet, J=7.2 Hz, 2H), 1.42-1.38 (m, 4H), 1.28-1.24 (m, 4H), 0.84 (t, J=7.2 Hz, 6H).

後処理

  1. temperatureunder reflux for 36 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customPurification by column chromatography (20% to 30% EtOAc—hexanes gradient)

出典と根拠

ORDレコード
ord-c63d7e8e07b74a9097795b3483174c46
出典データセット
uspto-grants-2014_03
特許番号
US08674137B2

反応ノート

読み込み中…