N-benzyl-2-(4-benzyloxy-3-tert-butylphenyl)-1-methyl-N-(benzyloxycarbonyl)-ethylamine → 2-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethylamine

HRID 1988298Notes

Reaction equation

HRID 1988298 reaction equation
C([N:8]([CH:19]([CH3:39])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[C:23]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:22]=1)C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[C:35]([C:23]1[CH:22]=[C:21]([CH2:20][CH:19]([NH2:8])[CH3:39])[CH:26]=[CH:25][C:24]=1[OH:27])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 2

HCID 21187419N-benzyl-2-(4-benzyloxy-3-tert-butylphenyl)-1-methyl-N-(benzyloxycarbonyl)-ethylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 211874322-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethylamineYield 96.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-benzyl-2-(4-benzyloxy-3-tert-butylphenyl)-1-methyl-N-(benzyloxycarbonyl)-ethylamine (2.35 g, 4.50 mmol) and 20% palladium hydroxide/carbon catalyst (0.50 g) in methanol (30 ml) was stirred in a hydrogen atmosphere overnight. The mixture was filtered to remove the catalyst and the filtrate was evaporated to remove the solvent under reduced pressure, giving 2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethylamine (T21) (0.90 g, 96%).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated
  4. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-3ee9c79c580a4c46b4e0b8eee5859d5b
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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