Sodium Bicarbonate → 2-Bromo-N-(tert-butoxycarbonyl)benzylamine

HRID 1786709Notes

Reaction equation

HRID 1786709 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[C:11](=[O:14])(O)[O-:12].[Na+]>C(OCC)(=O)C.O>[C:4]([O:12][C:11](=[O:14])[NH:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[Br:2])([CH3:7])([CH3:5])[CH3:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 27242022-Bromobenzylamine hydrochloride

Product 1

HCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromobenzylamine hydrochloride (5.00 g) and di-tert-butoxycarbonyl (5.39 g) in ethyl acetate (30 ml) was added saturated sodium bicarbonate solution (30 ml), and stirred at room temperature for 16 hours. The obtained reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a colorless liquid (6.48 g, 95%).

Workup

  1. customThe obtained reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d8d8511fd6714c77bb469f6797f331c4
Source dataset
uspto-grants-2009_03
Patent number
US07507753B2

Reaction notes

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