[Rac]-3-(4-benzyloxy-3-fluoro-phenyl)-2-isopropoxy-propionic acid ethyl ester → [Rac]-3-(3-fluoro-4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl ester

HRID 394306

Reaction equation

HRID 394306 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:22][CH:23]([CH3:25])[CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[C:9]([F:21])[CH:8]=1)[CH3:2]>[Pd].C1COCC1>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([O:22][CH:23]([CH3:25])[CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:21])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68617305[Rac]-3-(4-benzyloxy-3-fluoro-phenyl)-2-isopropoxy-propionic acid ethyl ester

Product 1

HCID 68616202[Rac]-3-(3-fluoro-4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl esterYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of 10% palladium on charcoal were added to a solution of 3.7 g of [rac]-3-(4-benzyloxy-3-fluoro-phenyl)-2-isopropoxy-propionic acid ethyl ester (10.26 mmol) in 30 ml of THF and the compound was stirred under an atmosphere of H2, at normal pressure and ambient temperature, until the absorption of gas stopped. After filtration of the catalyst and evaporation of the filtrate, 2.7 g of [rac]-3-(3-fluoro-4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl ester were obtained as colorless viscous oil (97.3% of theory).

Workup

  1. filtrationAfter filtration of the catalyst and evaporation of the filtrate

Sources & evidence

ORD record
ord-57fc810ee6c24904a01cb61137da40e9
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Linked notes

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