4-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol → N-[2-(4-Methoxymethylphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

HRID 434362Notes

Reaction equation

HRID 434362 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1.[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][OH:26])[CH:19]=1)[CH2:16][NH2:17]>C(O)C.[Pt]=O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:17][CH2:16][CH:15]([OH:14])[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][OH:26])[CH:19]=2)[CH3:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 129448344-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenolHCID 204938201-[4-(Methoxymethyl)phenyl]propan-2-one

Product 1

HCID 20493821N-[2-(4-Methoxymethylphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-methoxymethylphenyl)propan-2-one (0.46 g) and 2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl) ethanamine (0.45 g) in ethanol (50 ml) was refluxed 0.5 hours, cooled to ambient temperature and hydrogenated at atmospheric pressure using platinum oxide as catalyst. The solution was filtered, evaporated, the residue taken up in ethyl acetate and filtered again. Removal of the solvent gave an oil which was crystallised and recrystallised from benzene to give the title compound, mp 81°-92°, as a 53:47 mixture of diastereoisomers.

Workup

  1. temperaturewas refluxed 0.5 hours
  2. filtrationThe solution was filtered
  3. customevaporated
  4. filtrationfiltered again
  5. customRemoval of the solvent
  6. customgave an oil which
  7. customwas crystallised
  8. customrecrystallised from benzene

Sources & evidence

ORD record
ord-1a719f0f06d14871a0764471c37586ab
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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