Reaction #1726675

ord-65fe47f0889e4d5f97f4943399dee66e

Reaction equation

COC(=O)C(=O)c1ccccc1
methyl benzoyl formate
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
→
COC(=O)[C@H](O)c1ccccc1
(R)-methyl mandelate
Yield 87.5%

Reactants

COC(=O)C(=O)c1ccccc1
methyl benzoyl formate
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine

Reagents

[Ir]
Ir/C
[Ir]
Ir/C

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationfiltration
  2. 2
    Otherafter the reaction
  3. 3
    ConcentrationThe filtrate was concentrated
  4. 4
    Otherthe residue was purified

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110519B2uspto-grants-2012_02