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

HRID 580622Notes

Reaction equation

HRID 580622 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:26])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24]O)[CH:18]=2)[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[H][H]>C(O)C.C(Cl)(Cl)Cl.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:26])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH3:24])[CH:18]=2)[CH3:13])=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 2

HCID 19910569N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 20134197N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-(4-hydroxy-3-methylphenyl)ethanamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine (3.0 g) was hydrogenated in a mixture of ethanol (200 ml) and chloroform (20 ml) at 1 atmosphere and room temperature in the presence of 5% palladium on charcoal (150 mg) until hydrogen uptake was complete. The catalyst was removed and the product was recrystallised as the hydrochloride from ethyl acetate as a 32.5:67.5 mixture of diastereoisomers, mp 103°-107° (2.0 g). τ (d6DMSO) 8.88 (3H, d, J=6 Hz), 7.90 (3H, s), 6.10-7.20 (7H, m), 6.20 (3H, s), 5.02 (1H, m), 2.70-3.30 (3H, m), 2.62 (2H, d, J=8 Hz), 2.10 (2H, d, J=8 Hz), 0.62 (1H, br).

Workup

  1. customThe catalyst was removed
  2. customthe product was recrystallised as the hydrochloride from ethyl acetate as a 32.5:67.5 mixture of diastereoisomers, mp 103°-107° (2.0 g)

Sources & evidence

ORD record
ord-6a6aeb067cb64dd1b68cf7f6b39cd993
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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