Methanol → Tert-butyl 4-carbamimidoylpiperidine-1-carboxylate

HRID 1507501

Reaktionsgleichung

Reaktionsgleichung von HRID 1507501
O[NH:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].CO>[Ni].C(O)(=O)C>[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)(=[NH:2])[NH2:4]

Komponenten

5

Edukt 2

HCID 887MethanolHCID 178451986HCID 178451986, Verbindung

Produkt 1

HCID 44828660Tert-butyl 4-carbamimidoylpiperidine-1-carboxylateAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a 2-L round-bottom flask purged and maintained with an inert atmosphere of argon, was placed tert-butyl 4-(N-hydroxycarbamimidoyl)piperidine-1-carboxylate (46.5 g, 181.56 mmol, 1.00 equiv, 95%), methanol (1500 mL), acetic acid (20 mL), and Raney-Ni (13 g). The reaction system was bubbled for 5 times with hydrogen. The resulting mixture was stirred for 3 h at 50° C. in an oil bath. The solids were filtered out. The resulting solution was concentrated under vacuum to afford 40 g of tert-butyl 4-carbamimidoylpiperidine-1-carboxylate as yellow green crude oil, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 278.

Aufarbeitung

  1. customInto a 2-L round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of argon
  3. customThe reaction system was bubbled for 5 times with hydrogen
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting solution was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-07e5935378e142639bd1e691f0f835f7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221809B2

Verknüpfte Notizen

Wird geladen…