2-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine → 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

HRID 2401106

Reaktionsgleichung

Reaktionsgleichung von HRID 2401106
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])[CH2:12]2)[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])[CH2:12]2)[N:3]=1

Komponenten

4

Edukt 1

HCID 674786772-Methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine

Produkt 1

HCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amineAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]-3-nitro-pyridine (2 g, 6.89 mmol) and 10% Pd/C (200 mg) in ethanol (40 mL) was shaken on a parr shaken under 50 psi H2 for 18 h. The reaction mixture was filtered through a celite pad and concentrated to afford a dark red oil which was then purified by flash column chromatography (10% MeOH/CH2Cl2) to afford 580 mg (32% yield) of the title compound as an oil.

Aufarbeitung

  1. stirringshaken under 50 psi H2 for 18 h
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. concentrationconcentrated
  4. customto afford a dark red oil which
  5. customwas then purified by flash column chromatography (10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b137839800a4483896bcf2925b3b5143
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796278B2

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