1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole → (S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

HRID 2381286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381286
[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[N:9]2)[CH2:4][O:3]1.[H][H]>CO.[Pd]>[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)[CH2:4][O:3]1

Komponenten

5

Edukt 2

HCID 593449571-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57346939(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amineAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole (348.4 mg, 1.53 mmol) in methanol (10 mL, 0.15M) in a high pressure reaction bottle was treated with 10% palladium on activated carbon (19.5 mg). The mixture was placed on a Parr shaker and exposed to hydrogen (40 psi) overnight. After this time, the reaction mixture was filtered through a pad of diatomaceous earth and rinsed with ethanol. The filtrate was concentrated in vacuo to afford 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (237.4 mg, 1.20 mmol) as a viscous, yellow oil. The material was used without further purification.

Aufarbeitung

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of diatomaceous earth
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-667fb891f3e84ef3923cfea46d046e58
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258134B2

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