Sodium Carbonate → tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

HRID 1993669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993669
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>C(O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Dissolve N-Boc-4-aminopiperidine (0.9 g, 4.8 mmol) in dry ethanol and add solid sodium carbonate (0.8 g, 7.9 mmol) at 0° C., followed by 2-chloro-5-nitro-pyridine (0.6 g, 3.9 mmol). Stir the solution at room temperature overnight, then heat the solution at 9° C. for 6 hours. Stir at room temperature overnight. Evaporate the solvent under reduced pressure and partition the crude mixture between EtOH and water. Extract with EtOAc and wash the organic layer with saturated aq. sodium chloride solution. Combine organic layers and dry over MgSO4. Filter and evaporate the solvent in order to obtain 4-(5-Nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. temperatureheat the solution at 9° C. for 6 hours
  2. stirringStir at room temperature overnight
  3. customEvaporate the solvent under reduced pressure
  4. custompartition the crude mixture between EtOH and water
  5. extractionExtract with EtOAc
  6. washwash the organic layer with saturated aq. sodium chloride solution
  7. dry with materialCombine organic layers and dry over MgSO4
  8. filtrationFilter
  9. customevaporate the solvent in order

Quellen und Nachweise

ORD-Eintrag
ord-5889c8e2a7d948fdb556c226a1f8094e
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652015B2

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