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

HRID 1383735Notes

Reaction equation

HRID 1383735 reaction equation
C([NH:8][CH:9]([CH3:39])[CH:10](C(OCC1C=CC=CC=1)=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[C:13]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:12]=1)C1C=CC=CC=1.[H][H]>CO.[PdH2]>[C:25]([C:13]1[CH:12]=[C:11]([CH2:10][CH:9]([NH2:8])[CH3:39])[CH:16]=[CH:15][C:14]=1[OH:17])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 68869127N-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-methylethylamine

Reagents, catalysts & solvents 2

HCID 13628823Pd(II)-hydrideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2.35 g (4.50 mmol) of N-benzyl-2-(4-benzyloxy-3-tert-butylphenyl)-1-methyl-N-(benzyloxycarbonyl)ethylamine and 0.50 g of a 20% palladium hydride on carbon catalyst in methanol (30 ml) was stirred overnight in a hydrogen atmosphere. After filtering off the catalyst, the solvent was distilled off under reduced pressure to give 2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethylamine in the amount of 0.90 g (96%).

Workup

  1. filtrationAfter filtering off the catalyst
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e3ed5a31da1140ed9762ae0d47ec8915
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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