methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate → (4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol

HRID 657845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657845
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([NH2:21])=[CH:19][C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])=[N:17]2)=[CH:12][CH:11]=1>O1CCCC1>[NH2:21][C:20]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)[N:17]=[C:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=1

Komponenten

4

Edukt 2

HCID 2973426methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 58532567(4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanolAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminium hydride (1M in tetrahydrofuran, 1.83 mL, 1.83 mmol) was added to an ice-cold solution of 4-[5-amino-3-(1,1-dimethylethyl)-1H-pyrazol-yl]-benzoic acid methyl ester [(0.25 g, 0.92 mmol), WO2004060306, p134] in tetrahydrofuran (5 mL), and the mixture was stirred at 0° C. for 1 hour. The reaction was then quenched with water (0.35 mL) and 1M sodium hydroxide solution (0.35 mL) followed by further water (1 mL). The mixture was then extracted with diethyl ether, (10 mL) and the organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as red oil in 98% yield, 220.1 mg.

Aufarbeitung

  1. customThe reaction was then quenched with water (0.35 mL) and 1M sodium hydroxide solution (0.35 mL)
  2. extractionThe mixture was then extracted with diethyl ether, (10 mL)
  3. dry with materialthe organic solution was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e6bfe3a2600b4ebe91c4826e37b1ed93
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076356B2

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