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

HRID 1643858Notes

Reaction equation

HRID 1643858 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:2]1.[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O.CCOCC>C1COCC1>[C:14]([O:13][C:12](=[O:18])[NH:11][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([Br:19])[CH:6]=2)[NH:1][CH2:2]1)([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinolineHCID 21124087Pyridiniumtribromide

Product 1

HCID 17758659tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamateYield 1,863.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1A (2.7 g, 10.9 mmol) in THF (50 mL) at RT was added dropwise a solution of pyridinium tribromide (3.83 g, 0.41 mmol) in THF (50 mL). After addition, the reaction mixture was stirred for 15 min, then water (60 mL) and ether (60 mL) added. The aqueous layer was separated, and extracted with EtOAc (2×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexane to give the title compound (2.5 g, 70% yield) as a white solid.

Workup

  1. additionAfter addition
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with EtOAc (0 to 50%) in hexane

Sources & evidence

ORD record
ord-d9b6bb1a259a4a22b628eb8d6a9854ed
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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