Methyl 2-oxo-3-phenylpropanoate → Methyl 2-hydroxy-3-phenylpropanoate

HRID 1357342Notes

Reaction equation

HRID 1357342 reaction equation
[O:1]=[C:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[H][H]>C1COCC1>[OH:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 562359Methyl 2-oxo-3-phenylpropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-oxo-3-phenylpropionate (16d, R18=Ph, R19=methyl) was hydrogenated according to General Procedure B in THF at 20.7 barg (300 psig) hydrogen at ambient temperature using bis(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (2.3 mg; 5 μmol; 0.01 equiv) and ligand (S,R)-2e (3.1 mg; 6 μmol; 0.012 equiv) for 6 hours to afford methyl 2-hydroxy-3-phenylpropionate (17d, R18=Ph, R19=methyl) with 83.2% ee as determined by chiral GC analysis.

Workup

  1. customfor 6 hours

Sources & evidence

ORD record
ord-d7b4d0f134de43c09b4bb1a5970247d5
Source dataset
uspto-grants-2003_07
Patent number
US06590115B2

Reaction notes

Loading…