Triethylamine → (S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol

HRID 45992

Reaktionsgleichung

Reaktionsgleichung von HRID 45992
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28](Cl)(=[O:30])=[O:29])=[C:23]([CH3:32])[CH:22]=1>ClCCl>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH3:32])[C:24]([S:28]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C@H:2]2[CH2:10][OH:11])(=[O:29])=[O:30])=[C:25]([CH3:27])[CH:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6951186(S)-(+)-2-IndolinemethanolHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Produkt 1

HCID 57989609(S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a cold (0° C.) solution of (S)-indolin-2-ylmethanol (4.60 mmol, 1.2 equiv.) and triethylamine (2.5 equiv.) in dichloromethane (20 ml) was added dropwise 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (3.83 mmol, 1.0 equiv.) in dichloromethane (5 ml) and the reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane, washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography. Yield: 72%.

Aufarbeitung

  1. washwashed successively with water and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe crude product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-22a154f28b114d2ea8d063a8e694a9b1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541573B2

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