HCID 86633705, compound → HCID 57288795, compound

HRID 887940Notes

Reaction equation

HRID 887940 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][C@H:10]([C@H:15]([OH:17])[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:15]([OH:17])[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86633705HCID 86633705, compound

Product 1

HCID 57288795HCID 57288795, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (2R,3R)-2-[(2E)-3-phenyl-2-propen-1-yl]-3-hydroxybutanoate (42.0 g, 179.5 mmol) in 400 mL of methanol is treated with 400 mg of 10% palladium on carbon. The resulting suspension is repeatedly evacuated and purged with a hydrogen balloon, then stirred under 1 atmosphere pressure of hydrogen gas for 16 h. The catalyst is filtered and the filtrate is concentrated in vacuo to provide methyl (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxybutanoate as an oil (42.2 g, 100% yield).

Workup

  1. customThe resulting suspension is repeatedly evacuated
  2. custompurged with a hydrogen balloon
  3. filtrationThe catalyst is filtered
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-e6c30621c7184658b5535ba0978b0338
Source dataset
uspto-grants-2012_08
Patent number
US08247451B2

Reaction notes

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