Ethanol → (2S)-2-methylbutanedioic acid

HRID 1470769Notes

Reaction equation

HRID 1470769 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].C(O)C.[H][H]>O1CCCC1>[CH3:3][C@@H:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 811Itaconic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 6950476(2S)-2-methylbutanedioic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of an itaconic acid (40.9 mg, 0.314 mmol) dissolved in tetrahydrofuran (THF) (0.3 mL) and ethanol (EtOH) (0.3 mL) is added to an autoclave in which the catalyst obtained in Preparation Example 7 was added. After replacing the atmosphere to hydrogen gas, it was stirred for 18 hours at reaction temperature of 50° C. under 3 atm pressure of hydrogen. After the reaction, it was cooled down to be room temperature, and the catalyst was filtered in the atmosphere to recover thereof and washed with THF (1 mL) three times. The solvent was concentrated from the filtrate, and the desired (S)-2-methylsuccinic acid was obtained. The yield thereof measured by NMR was >99%, and the optical purity thereof was >90% ee.

Workup

  1. customobtained in Preparation Example 7
  2. additionwas added
  3. customAfter the reaction, it
  4. temperaturewas cooled down
  5. customto be room temperature
  6. filtrationthe catalyst was filtered in the atmosphere
  7. customto recover
  8. washwashed with THF (1 mL) three times
  9. concentrationThe solvent was concentrated from the filtrate

Sources & evidence

ORD record
ord-6747a112e7d04f659bbc053f81e9f41d
Source dataset
uspto-grants-2015_04
Patent number
US09006484B2

Reaction notes

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