2-{2-[4-(2-Methoxycarbonylethenyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol → 2-{2-[4-(2-Methoxycarbonylethyl)phenoxy]-1-methylethyl}amino-1-phenylethanol

HRID 1682695Notes

Reaction equation

HRID 1682695 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[CH:27]=[CH:26][C:10]([O:11][CH2:12][CH:13]([NH:15][CH2:16][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21](Cl)[CH:20]=2)[OH:18])[CH3:14])=[CH:9][CH:8]=1)=[O:4]>CO>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:27]=[CH:26][C:10]([O:11][CH2:12][CH:13]([NH:15][CH2:16][CH:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[OH:18])[CH3:14])=[CH:9][CH:8]=1)=[O:4]

Participants

3

Reactant 1

HCID 543845792-{2-[4-(2-Methoxycarbonylethenyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol

Product 1

HCID 218321972-{2-[4-(2-Methoxycarbonylethyl)phenoxy]-1-methylethyl}amino-1-phenylethanolYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.2 g of 2-{2-[4-(2-methoxycarbonylethenyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 53) were dissolved in 200 ml of methanol and hydrogenated by bubbling hydrogen through the solution at atmospheric pressure and at room temperature in the presence of 0.5 g of 10% w/w palladium-on-charcoal for 3 hours. The catalyst was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was dissolved in ethyl acetate, and the resulting solution was washed with an aqueous solution of potassium carbonate and with water, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent. The product thus obtained was recrystallized from a mixture of ethyl acetate and hexane, to give 1.2 g of the title compound as crystals, melting at 103°-104° C.

Workup

  1. customhydrogenated by bubbling hydrogen through the solution at atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. dissolutionThe concentrate was dissolved in ethyl acetate
  5. washthe resulting solution was washed with an aqueous solution of potassium carbonate and with water, in that order
  6. dry with materialafter which it was dried over anhydrous sodium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel
  9. customThe product thus obtained
  10. customwas recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-833bf0d21299457587019fa265cf0eb3
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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