HCID 20134171, compound → HCID 20134198, compound

HRID 1633092Notes

Reaction equation

HRID 1633092 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][C:19]=2[Cl:32])[OH:17])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]>C(O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=2[Cl:32])[OH:17])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 20134171HCID 20134171, compound

Product 1

HCID 20134198HCID 20134198, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(4-benzyloxy-2-chlorophenyl)-2-hydroxyethanamine was hydrogenated in ethanol at atmospheric pressure and room temperature in the presence of 5% palladium on charcoal. The catalyst was removed and the product was recrystallised as the hydrochloride from ethyl acetate as a 28:72 mixture of diastereoisomers, mp 194°-195°. τ (d6DMSO) 8.79 (3H, d, J=6 Hz), 6.20-7.50 (6H, m), 6.16 (3H, s), 4.67 (1H, m), 2.30-3.30 (5H, m), 2.07 (2H, d, J=8 Hz), 0.67 (1H, br).

Workup

  1. customThe catalyst was removed
  2. customthe product was recrystallised as the hydrochloride from ethyl acetate as a 28:72 mixture of diastereoisomers, mp 194°-195°

Sources & evidence

ORD record
ord-42f6e4559f6040be956a5751f78ee887
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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