Water → tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

HRID 1019676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019676
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:19])[CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinolineHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamateAusbeute 1.863,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of XXIII (2.7 g, 10.9 mmol) in THF was added dropwise a solution of pyridinium tribromide (3.83, 0.41 mmol) in 50 mL of THF at rt. The reaction mixture was stirred for 15 min before 60 mL of water was added into the flask. The aqueous phase was extracted with EtOAc. The combined organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography to give (6-bromo-1,2,3,4-tetrahydro-quinoline-3-yl)-carbamic acid tert-butyl ester XXIV (2.5 g, 70%) as white solid.

Aufarbeitung

  1. additionwas added into the flask
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washThe combined organic phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7fdb4c85ec1a48388b723a181969008f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716285B2

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