Water → (1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol

HRID 1814108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814108
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)=O.O>O1CCCC1>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:12]2[C:13]3[C:18](=[CH:17][C:16]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:15][CH:14]=3)[CH:19]=[C:11]2[CH2:9][OH:8])=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 684447041-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic Acid Methyl Ester

Produkt 1

HCID 22504394(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanolAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of lithium aluminum hydride (366 mg) in tetrahydrofuran (20 ml), a solution of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic acid methyl ester obtained in Example 27 (3) (1.86 g) in tetrahydrofuran (20 ml) was added dropwise at 0° C. under nitrogen atmosphere and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was poured into water, filtered through Celite and extracted with chloroform. The organic layer was washed with water and dried. The solvent was distilled off under reduced pressure to obtain (1-(4-fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol (1.8 g). To a solution of the resulting alcohol (1.8 g) in dichloromethane (100 ml) was added manganese dioxide (15.3 g) at 15 to 30° C. and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was filtered through Celite. The solvent was distilled off under reduced pressure to obtain 1.5 g (88.4%) of the desired product as a yellow powder.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d18c1d47eb1f4c508d962120715c500c
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875770B2

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