Butyl bromide → HCID 68485070, compound

HRID 1896973Notes

Reaction equation

HRID 1896973 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH3:28]>CC(C)=O>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 68485743HCID 68485743, compound

Product 1

HCID 68485070HCID 68485070, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution in acetone (240 ml), of 2-(3-hydroxyphenyl)-(tert-butoxycarbonyl)ethylamine obtained in Step 1, K2CO3 (19.8 g) and 1-bromobutane (15 ml) were added. The suspension was refluxed for 3 days and the solvent was evaporated under reduced pressure. The residue was dissolved in H2O (200 ml) and extracted with CH2Cl2 (2×200 ml). The solvent was eliminated under reduced pressure and the residue was purified by flash chromatography (petroleum ether/EtOAc 85:15) affording 1 (11.3 g, 81% over 3 steps) of the title compound as colorless oil.

Workup

  1. temperatureThe suspension was refluxed for 3 days
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in H2O (200 ml)
  4. extractionextracted with CH2Cl2 (2×200 ml)
  5. customthe residue was purified by flash chromatography (petroleum ether/EtOAc 85:15)

Sources & evidence

ORD record
ord-982a0896c5c44837981359e721fcf6c8
Source dataset
uspto-grants-2013_08
Patent number
US08519000B2

Reaction notes

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