Tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate → Tert-butyl 3-(methylamino)benzylcarbamate

HRID 2071007Notes

Reaction equation

HRID 2071007 reaction equation
[CH2:1]([N:8](C)[C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:1][NH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 1

HCID 68670737Tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate

Product 1

HCID 57763264Tert-butyl 3-(methylamino)benzylcarbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

20% Pd(OH)2 0.076 g) was added to a stirred suspension of tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate (0.248 g, 0.76 mmol, 1 eq) in 10 ml EtOH. A H2 balloon was added. After stirring overnight the mixture was filtered through Celite. The filter cake was rinsed with EtOAc (×3). The organics were combined and the solvent was removed in vacuo to yield tert-butyl 3-(methylamino)benzylcarbamate.

Workup

  1. additionA H2 balloon was added
  2. filtrationwas filtered through Celite
  3. washThe filter cake was rinsed with EtOAc (×3)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-148f23d4ee9644468480518b4aae477d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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