Magnesium perchlorate → 2-Hydroxy-3-(4-methoxyindolin-1-yl)-3-phenylpropanol

HRID 1279493

反応式

HRID 1279493 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:7]2.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[O:23]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]1[CH2:25][OH:26]>CC#N.C([O-])(O)=O.[Na+]>[OH:23][CH:24]([CH:27]([N:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][OH:26]

参加物

6

反応物 3

HCID 24840Magnesium perchlorateHCID 89553(3-Phenyloxiranyl)methanolHCID 162444414-methoxy-2,3-dihydro-1H-indole

生成物 1

HCID 184284162-Hydroxy-3-(4-methoxyindolin-1-yl)-3-phenylpropanol

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 1.00 g (6.62 mmol) of 4-methoxyindoline (Gangjee et al., J. Med. Chem. 1997, 40, 479-485) and 1.90 g (8.51 mmol) of magnesium perchlorate in 20 mL of CH3CN was treated in a dropwise manner with a solution of 1.00 g (6.62 mmol) of 2,3-epoxy-3-phenyl-1-propanol (Ogata and Tomizawa, Bull. Chim. Soc. Jap. 1977, 50, 261-265) in 10 mL of CH3CN. The reaction was stirred at ambient temperature for 2.5 hours and was diluted with 30 mL of saturated aqueous NaHCO3. The organic layer was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The oil was purified by radial chromatography (SiO2; 10% then 20% then 30% EtOAc in hexanes) to afford 1.55 g (5.17 mmol; 78%) of the subtitled compound as a solid.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe oil was purified by radial chromatography (SiO2

出典と根拠

ORDレコード
ord-fba1dbd9606b4768b5f2bb98b07bc2bb
出典データセット
uspto-grants-2002_09
特許番号
US06448284B1

関連ノート

読み込み中…