Water → HCID 21948877, Verbindung

HRID 2054981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2054981
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:16]=[CH:17][C:18]([C:33]([F:36])([F:35])[F:34])([OH:32])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:22])[CH3:21])[N:7]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO.O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH:16][CH2:17][C:18]([C:33]([F:34])([F:35])[F:36])([OH:32])[CH2:19][C:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])([CH3:22])[CH3:21])[N:7]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21948882HCID 21948882, Verbindung

Produkt 1

HCID 21948877HCID 21948877, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution that consists of 170 mg (0.34 mmol) of 1-(2-(acetoxymethyl)quinolin-5-ylimino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol in 1.5 ml of methanol and 0.8 ml of tetrahydrofuran is mixed with 53 mg (1.38 mmol) of sodium borohydride. After 3 hours at room temperature, the reaction is halted by adding water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution and dried on sodium sulfate. After removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (0-100%), 94 mg (55% of theory) of the product is obtained.

Aufarbeitung

  1. extractionIt is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. customAfter removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (0-100%), 94 mg (55% of theory) of the product
  5. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-e71d9fa673074c77bf3ff13108ac51e6
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07329753B2

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