Triethylamine → (R)-1-(benzyl(6-bromo-3-nitropyridin-2-yl)amino)propan-2-ol

HRID 1485681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485681
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[N:3]=1.C(N(CC)CC)C.[CH2:19]([NH:26][CH2:27][C@H:28]([OH:30])[CH3:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([N:26]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Br:11])[N:3]=1)[CH2:27][C@H:28]([OH:30])[CH3:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5550532,6-Dibromo-3-nitropyridineHCID 964915(R)-1-(Benzylamino)-2-propanol

Produkt 1

HCID 118079393(R)-1-(benzyl(6-bromo-3-nitropyridin-2-yl)amino)propan-2-olAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2,6-Dibromo-3-nitropyridine (2.59 g, 9.20 mmol) and triethylamine (2.70 mL, 19.37 mmol) were added to a solution of (R)-1-(benzylamino)propan-2-ol (1.6 g, 9.68 mmol) in ethanol (35 mL). The solution was stirred at rt for 17 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (25 mL). The layers were separated, and the organic layer was washed with 5% aqueous sodium chloride solution (25 mL). The ethyl acetate layer was concentrated under reduced pressure to afford an orange syrup. The crude product was purified by column chromatography on silica gel (eluting with 5:1 hexanes-ethyl acetate followed by 3:1 hexanes-ethyl acetate) to afford (R)-1-(benzyl(6-bromo-3-nitropyridin-2-yl)amino)propan-2-ol (3.01 g, 85%) as a bright yellow syrup. MS (ESI, pos. ion) m/z 388, 390 [M+Na]+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution (25 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with 5% aqueous sodium chloride solution (25 mL)
  5. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  6. customto afford an orange syrup
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 5:1 hexanes-ethyl acetate followed by 3:1 hexanes-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-87f0bcd6810d4793a32b763dd95258f3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422281B2

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