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

HRID 1279493

반응식

HRID 1279493 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fba1dbd9606b4768b5f2bb98b07bc2bb
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448284B1

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