4-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester → 4-(2-tert-Butoxycarbonyl-ethyl)-3-methyl-benzoic Acid Methyl Ester

HRID 220821Notes

Reaction equation

HRID 220821 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:6]([CH3:19])[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[C:6]([CH3:19])[CH:5]=1

Participants

4

Reactant 1

HCID 575553844-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575553714-(2-tert-Butoxycarbonyl-ethyl)-3-methyl-benzoic Acid Methyl EsterYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic acid methyl ester from Example E30.1 (4.00 g, 14.5 mmol) was dissolved in methanol (100 ml) and hydrogenated over 10% Pd/C catalyst (480 mg) for 5 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo to yield the title compound (3.41 g, 84%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6a9790a965094482afe459ac5035ee68
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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