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

HRID 1639493Notes

Reaction equation

HRID 1639493 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>[Ir].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 2

HCID 84835Methyl phenylglyoxalateHCID 101744Cinchonidine

Product 1

HCID 2724623(R)-(-)-Methyl mandelateYield 87.5%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalyst2×HCID 1140TolueneSolvent

Procedure

Five percent Ir/C (38.4 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 were agitated for five hours at room temperature under hydrogen at a pressure of 50 atmospheres. The cross-linked Ir/C cluster composition was removedby filtration after the reaction. The filtrate was concentrated, and the residue was purified using PTLC to obtain (R)-methyl mandelate (145.4 mg, 87.5% yield). The asymmetric yield was 2.0% ee.

Workup

  1. filtrationfiltration
  2. customafter the reaction
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-65fe47f0889e4d5f97f4943399dee66e
Source dataset
uspto-grants-2012_02
Patent number
US08110519B2

Reaction notes

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