4-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol → HCID 20533264, compound

HRID 1758975Notes

Reaction equation

HRID 1758975 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[OH:17][CH:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH2:28][OH:29])[CH:22]=1)[CH2:19][NH2:20]>C(O)C.[Pd]>[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:20][CH2:19][CH:18]([OH:17])[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH2:28][OH:29])[CH:22]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 129448344-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenolHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

Product 1

HCID 20533264HCID 20533264, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-carbomethoxymethoxyphenyl)propan-2-one (1.5 g) and 2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine (1.23 g) in ethanol (80 ml) was refluxed 0.5 hours, cooled to ambient temperature, 10% Pd/C added and the mixture hydrogenated at 75 psi and 50°-60° for 8 hours. 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, 0.47 g, mp 60°-63° as a 52:48 mixture of diastereoisomers. τ(d6DMSO) 9.1 (3H, d, J=6 Hz), 6.6-7.8 (5H, m), 6.4 (3H, s), 5.72 (1H, t, J=6 Hz), 5.54 (2H, s), 5.3 (2H, s), 7.2-6.4 (7H, m), 7.6-5.5 (4H, broad, disappears with D2O).

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-5eeccd6edbfa479b8dba6b830c862741
Source dataset
uspto-grants-1982_07
Patent number
US04338333

Reaction notes

Loading…