Water → HCID 7174672, compound

HRID 1667389Notes

Reaction equation

HRID 1667389 reaction equation
O.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:13])[C:10]([OH:12])=[O:11]>[Ir].C(O)=O>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@H:9]([OH:13])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 962WaterHCID 12385697HCID 12385697, compound2×

Product 1

HCID 7174672HCID 7174672, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 284Formic AcidSolvent

Procedure

A mixed solvent (volume ratio=1:1, 5 mL) of water and formic acid and a chiral iridium aqua complex represented by the formula (12-R) (0.5 mol % relative to 2-methylphenylglyoxylic acid) were mixed, and 2-methylphenylglyoxylic acid (1 mmol) was added to the obtained solution at room temperature. The obtained mixture was stirred at room temperature to carry out asymmetric transfer hydrogenation. After confirming the disappearance of 2-methylphenylglyoxylic acid by thin layer chromatography, the reaction was quenched with brine (20 mL). The reaction mixture was subjected to extraction treatment (three times) with ethyl acetate (20 mL), and the obtained organic layers were combined. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1) to give the corresponding (R)-2-(2-methylphenyl)-2-hydroxyacetic acid. Yield 95%, optical purity 83% e.e.

Workup

  1. additionwere mixed
  2. customthe reaction was quenched with brine (20 mL)
  3. extractionThe reaction mixture was subjected to extraction treatment (three times) with ethyl acetate (20 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-b36ee8b4e8df418eaf77ace539fe48b1
Source dataset
uspto-grants-2011_10
Patent number
US08044224B2

Reaction notes

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