HCID 17819224, compound → HCID 17819212, compound

HRID 1988297Notes

Reaction equation

HRID 1988297 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:18](C(OCC2C=CC=CC=2)=O)[CH3:19])[CH3:17])=[CH:11][C:10]=1[C:30]([CH3:33])([CH3:32])[CH3:31])C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[C:30]([C:10]1[CH:11]=[C:12]([CH2:15][CH:16]([NH:18][CH3:19])[CH3:17])[CH:13]=[CH:14][C:9]=1[OH:8])([CH3:32])([CH3:31])[CH3:33]

Participants

5

Reactant 2

HCID 17819224HCID 17819224, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17819212HCID 17819212, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-(4-benzyloxy-3-tert-butylphenyl)-N-benzyloxycarbonyl-N-methyl-1-methylethylamine (3.30 g, 7.35 mmol) and 20% palladium hydroxide/carbon catalyst (350 mg) in methanol (100 ml) was stirred in a hydrogen atmosphere for 1.5 hours. 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)-N-methyl-1-methylethylamine (T20) (1.62 g, 100%).

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-2bda898e707242b9bb4ad10118cc8c86
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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