(R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate → (R)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid

HRID 1487181Notes

Reaction equation

HRID 1487181 reaction equation
[CH:1]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])([C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C@H:2]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:3]>CO.[Pd]>[CH2:7]([O:6][C:4](=[O:5])[C@@H:2]([CH:1]([C:19]([OH:21])=[O:20])[C:9]([OH:11])=[O:10])[CH3:3])[CH3:8]

Participants

4

Reactant 1

HCID 86699677(R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

Product 1

HCID 86699678(R)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of (R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate (11 g, 0.029 mol) in MeOH (500 ml) was added Pd/C (wet, 2 g), and then the mixture was stirred under hydrogen atmosphere at room temperature overnight. After filtered the Pd/C, the solvent was removed under reduced pressure to afford (R)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid, which was purified by silica gel chromatography (3.5 g, 60%).

Workup

  1. filtrationAfter filtered the Pd/C
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c78689f8b78246f08a367ad6a6628e75
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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