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

HRID 2234243Notes

Reaction equation

HRID 2234243 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 tert-butyl 1,2,3,4-tetrahydroquinolin-3-yl-carbamate (2.7 g, 10.9 mmol), prepared as described in Example 1A, 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 saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexanes 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 saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with EtOAc (0 to 50%) in hexanes

Sources & evidence

ORD record
ord-360007701e354d049d4eb91702bac854
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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