Methanol → 3-(5-Fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

HRID 1867233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867233
[BH4-].[Na+].CO.[F:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:28])[C:9]([CH3:27])([CH3:26])[N:10]=[C:11]2[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>O>[F:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]([OH:28])[C:9]([CH3:26])([CH3:27])[N:10]=[C:11]2[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 231608453-(5-Fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

Produkt 1

HCID 231608883-(5-Fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolineAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium borohydride (103 mg) was added to a methanol (8 mL) solution of 3-(5-fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (300 mg, 0.9 mmol) followed by stirring for 2.5 hours at room temperature, pouring water, extracting with ethyl acetate, and applying the resulting residue to chromatography to obtain 215 mg (yield 74%) of the target compound.

Aufarbeitung

  1. extractionextracting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3557a81738e747a3b53b9fbb62f170a1
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632783B2

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