(2S)-3-(4-benzyloxy-2,6-dimethyl-phenyl)-2-ethoxy-propionic acid methyl ester → (2S)-2-ethoxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester

HRID 2215245Notes

Reaction equation

HRID 2215245 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([O:22][CH2:23][CH3:24])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13]CC2C=CC=CC=2)=[CH:8][C:7]=1[CH3:21]>[Pd]>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([O:22][CH2:23][CH3:24])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[CH3:21]

Participants

3

Reactant 1

HCID 68616291(2S)-3-(4-benzyloxy-2,6-dimethyl-phenyl)-2-ethoxy-propionic acid methyl ester

Product 1

HCID 68616541(2S)-2-ethoxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In analogy to the procedure described in example 46 b], (2S)-3-(4-benzyloxy-2,6-dimethyl-phenyl)-2-ethoxy-propionic acid methyl ester was hydrogenated over 10% palladium on charcoal to give (2S)-2-ethoxy-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester as colorless liquid.

Sources & evidence

ORD record
ord-f9847ee90cd046a7b6fa30dcc4e83776
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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