Methyl phenylglyoxalate → (R)-(-)-Methyl mandelate

HRID 1639491Notes

Reaction equation

HRID 1639491 reaction equation
[CH3:1][O:2][C:3]([C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[O:4].C=C[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C4C(=CC=CC=4)N=CC=3)N(CC2)C1.[H][H]>C1(C)C=CC=CC=1>[C:3]([O:2][CH3:1])(=[O:4])[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6]

Participants

5

Reactant 3

HCID 84835Methyl phenylglyoxalateHCID 101744CinchonidineHCID 178418361HCID 178418361, compound

Product 1

HCID 2724623(R)-(-)-Methyl mandelateYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The cross-linked Ir—Au cluster composition obtained in Example 12 (10.0 mg), methyl benzoyl formate (164.2 mg, 1.0 mmole), (−)cinchonidine (3.8 mg, 0.013 mmole) and toluene (5 ml) were mixed in an autoclave and agitated for hie hours at room temperature in a hydrogen atmosphere at a pressure of 50 atmospheres. The cross linked Ir—Au cluster composition was removed by filtration after the reaction. The filtrate was concentrated, and the residue was purified using PTLC to obtain (R)-methyl mandelate (160.5 mg, 96.5% yield). The asymmetric yield was 52.9% ee.

Workup

  1. additionwere mixed in an autoclave
  2. customwas removed by filtration
  3. customafter the reaction
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-27174e87f6554b64ae6773126b6d965c
Source dataset
uspto-grants-2012_02
Patent number
US08110519B2

Reaction notes

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