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

HRID 1639489Notes

Reaction equation

HRID 1639489 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 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The cross-linked Ir cluster composition obtained in Example 10 (14.4 mg, 0.01 mmole), 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 five hours at room temperature in a hydrogen atmosphere at 50 atmospheres pressure. The cross linked Ir 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 (147.1 mg, 88.5% yield). The asymmetric yield was 47.1% 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-082ecab26f0a42cfaf1b23d805743005
Source dataset
uspto-grants-2012_02
Patent number
US08110519B2

Reaction notes

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