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

HRID 1641788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1641788
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 782402-Bromo-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-bromo-5-nitro-pyridine (5 g, 24.6 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25 mmol), and triethylamine (5 mL) in N,N-dimethylformamide (30 mL) was stirred at 90° C. for 14 h. The reaction mixture was then partitioned between water and ethyl acetate, and the two layers were separated. The aqueous layer was extracted with ethyl acetate three times. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography to give 7.15 g (90%) 4-(5-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. LCMS calcd for C15H22N4O4 (m/e) 322, obsd 323 (M+H).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cc19b822469c4bf09675bc9b5045b96a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08115011B2

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