(2S)-3-(4-Benzyloxy-2-methyl-phenyl)-2-ethoxy-propionic acid methyl ester → (S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester

HRID 1064880Notes

Reaction equation

HRID 1064880 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([O:21][CH2:22][CH3:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][C:7]=1[CH3:20]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([O:21][CH2:22][CH3:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:20]

Participants

4

Reactant 1

HCID 68615603(2S)-3-(4-Benzyloxy-2-methyl-phenyl)-2-ethoxy-propionic acid methyl ester

Product 1

HCID 68616579(S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2S)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-propionic acid methyl ester (3.6 g, 11 mmol) in methanol (300 ml) was hydrogenated over 10% palladium on charcoal (1 g) at ambient temperature for 2 h. The catalyst was filtered off and the solvent evaporated under reduced pressure to give 2 g (8.4 mmol, 77%) of the title compound as yellow liquid which was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-f80bcc3b1fa6404299ebaa3371a89bcb
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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