Water → HCID 22736936, Verbindung

HRID 50861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50861
[F:1][C:2]1[C:11]([C:12](=[O:29])[CH2:13][N:14]2[CH2:19][CH2:18][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[C:11]([CH:12]([OH:29])[CH2:13][N:14]2[CH2:15][CH2:16][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22736931HCID 22736931, Verbindung

Produkt 1

HCID 22736936HCID 22736936, VerbindungAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one (630 mg, 1.5 mmol) and sodium borohydride (57 mg, 1.5 mmol) in ethanol (17 ml) was stirred at room temperature overnight. To the mixture was added water and extracted with dichloromethane. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (dichloromethane/methanol=10/1) to afford 5-Fluoro-6-[1-hydroxy-2-[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]ethyl]-3,4-dihydroquinolin-2(1H)-one as a yellow solid (220 mg).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-4a7666dd809b4aaeb833848863166315
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713490B2

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