Methyl 3-oxo-3-phenylpropanoate → Methyl (3S)-3-hydroxy-3-phenylpropanoate

HRID 2186493Notes

Reaction equation

HRID 2186493 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[OH:8][C@H:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

3

Reactant 1

HCID 348462Methyl 3-oxo-3-phenylpropanoate

Product 1

HCID 6993014Methyl (3S)-3-hydroxy-3-phenylpropanoateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1 liter autoclave was charged a mixture of 0.84 g of (1.0 mmol) of Ru2Cl4((R)-Tol-BINAP)2.NET3, 178 g (1.00 mol) of methyl benzoylacetate, and 500 ml of methanol, and the mixture was stirred at 50° C. under a hydrogen pressure of 1000 kPa for 16 hours. The solvent was evaporated under reduced pressure, and the residue was distilled under reduced pressure (99° C./100 Pa.) to yield 171 g (95%) of the title compound as liquid. Optical purity: 87%e.e.

Workup

  1. additionIn a 1 liter autoclave was charged
  2. customThe solvent was evaporated under reduced pressure
  3. distillationthe residue was distilled under reduced pressure (99° C./100 Pa.)

Sources & evidence

ORD record
ord-f82921ee905f44ebaf940fc2741baaf2
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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