Methyl 4-(2-oxopropyl)benzoate → N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

HRID 580627Notes

Reaction equation

HRID 580627 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[OH:15][CH:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][OH:27])[CH:20]=1)[CH2:17][NH2:18]>C(O)C.[Pd].C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:18][CH2:17][CH:16]([OH:15])[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH2:26][OH:27])[CH:20]=2)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 2

HCID 11137970Methyl 4-(2-oxopropyl)benzoateHCID 129448344-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol

Product 1

HCID 19910569N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamineYield 43%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-carbomethoxyphenyl)propan-2-one (70 g) and 2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine (66.7 g) in ethanol (1750 cm3) was stirred under reflux for 4 hours. The solution was cooled and added to a suspension of 10% palladium on charcoal, (Johnson Matthey type 87L), (20 g) in ethanol (50 cm3) and the resulting mixture hydrogenated at 90 psi and 50°-55° for 18 hours. The mixture was filtered through a Claraid bed, the residue washed with ethanol (about 500 cm3) and the filtrate evaporated under reduced pressure to yield a viscous gum. The gum was dissolved in hot ethyl acetate (100 cm3) and decanted from a small amount of residual brown oil. On standing a white solid crystallised which was filtered off, washed with diethyl ether (about 100 cm3) and dried to give the title compound 56.3 g (43%), mp 139°-141°. (13C NMR: indicated this to be a 7:3 mixture of diastereoisomers). On standing two further crops of the title compound crystallised from the filtrate giving a total yield of 84.7 g (64.7%).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe solution was cooled
  3. filtrationThe mixture was filtered through a Claraid bed
  4. washthe residue washed with ethanol (about 500 cm3)
  5. customthe filtrate evaporated under reduced pressure
  6. customto yield a viscous gum
  7. customdecanted from a small amount of residual brown oil
  8. customcrystallised which
  9. filtrationwas filtered off
  10. washwashed with diethyl ether (about 100 cm3)
  11. customdried

Sources & evidence

ORD record
ord-8c51528be424463584fc516a9f167a44
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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