Methyl 3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2,2-dimethylpropanoate → Methyl 3-(3-carboxy-4-methoxyphenyl)-2,2-dimethylpropanoate

HRID 1634525Notes

Reaction equation

HRID 1634525 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[C:9]([C:11]1[CH:12]=[C:13]([CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])([OH:10])=[O:8]

Participants

5

Reactant 1

HCID 11057401Methyl 3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2,2-dimethylpropanoate

Product 1

HCID 10923463Methyl 3-(3-carboxy-4-methoxyphenyl)-2,2-dimethylpropanoateYield 125.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2,2-dimethylpropanoate (310 mg, 0.870 mmol) was dissolved in 7 ml of mixed solvent of ethanol with tetrahydrofuran at a ratio of 1:1, 10% palladium on activated carbon (20 mg) was added thereto, and normal pressure hydrogenation was conducted for 5 hours. After completion of the reaction, catalyst was filtered and the filtrate was concentrated to obtain 290 mg (90%) of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. customAfter completion of the reaction, catalyst
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bb04c12890e043c1b6d70ca54ffb507e
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

Loading…