HCID 178501201, Verbindung → HCID 178501200, Verbindung

HRID 518595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518595
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1)([O-])=O>[Pd].CCO>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16]1

Komponenten

4

Edukt 1

HCID 178501201HCID 178501201, Verbindung

Produkt 1

HCID 178501200HCID 178501200, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(3-nitropyridin-4-ylamino)cyclohexanecarboxylate (1.1 g, 3.94 mmol) and Pd/C (10% wt) (0.419 g, 0.394 mmol). EtOH (16 mL) was added, and the reaction mixture was purged with nitrogen 3 times. A H2-filled balloon was attached to the top of the flask, and the mixture stirred at RT for 2 hours. The reaction mixture was diluted with EtOH and filtered through Celite® brand filter aid. The pad was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL). The filtrate was concentrated to dryness to afford cis-methyl 4-(3-aminopyridin-4-ylamino)cyclohexanecarboxylate as a purple oil. (0.9 g, 92.0% yield). MS m/z=250.2 [M+H]. Calc'd for C13H19N3O2: 249.2.

Aufarbeitung

  1. customthe reaction mixture was purged with nitrogen 3 times
  2. additionA H2-filled balloon
  3. additionThe reaction mixture was diluted with EtOH
  4. filtrationfiltered through Celite® brand
  5. filtrationfilter aid
  6. washThe pad was washed with DCM (50 mL), EtOH (50 mL), and MeOH (50 mL)
  7. concentrationThe filtrate was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d40edc173bb64fcc96c4e8d329ea9dd7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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