3-Fluoro-4-methylaniline → (RS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(3-fluoro-4-methyl-phenylamino)-butan-2-ol

HRID 1511806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511806
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH3:22])[NH2:18]>CC#N>[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][NH:18][C:17]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:15]([F:14])[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 99573-Fluoro-4-methylanilineHCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

Produkt 1

HCID 66954684(RS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(3-fluoro-4-methyl-phenylamino)-butan-2-olAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

LiClO4 (6.31 g, 60 mmol) was added to a solution of (RS)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (4 g, 20 mmol, prepared according to Heterocycles (1987), 25(1), 329-32) in MeCN (60 mL). 3-Fluoro-4-methylaniline (2.28 g, 18 mmol) was added and the mixture was stirred at 50° C. for 5 h. The solvent was removed under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2) to afford the title intermediate as brown oil (5.56 g, 86%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2)

Quellen und Nachweise

ORD-Eintrag
ord-af679ec97c2d4bd9942597c02c944a7e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217029B2

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