HCID 15083844, compound → HCID 53982593, compound

HRID 636018Notes

Reaction equation

HRID 636018 reaction equation
[CH3:1][C:2](=[CH2:12])[CH2:3][C@H:4]([C@H:9]([OH:11])[CH3:10])[C:5]([O:7][CH3:8])=[O:6]>CCOC(C)=O.[Pd]>[CH3:1][CH:2]([CH3:12])[CH2:3][C@H:4]([C@H:9]([OH:11])[CH3:10])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 15083844HCID 15083844, compound

Product 1

HCID 53982593HCID 53982593, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (2R,3R)-2-(2-methyl-2-propen-1-yl)-3-hydroxybutanoate (8.1 g, 47.1 mmol) in 85 mL of EtOAc is treated with 800 mg of 10% palladium on carbon and the mixture is evacuated and purged with nitrogen. The heterogeneous solution is stirred under 52 psi of hydrogen for 1.5 h. Filtration and concentration of the filtrate in vacuo affords 7.99 g (96%) of methyl (2R,3R)-2-(2-methyl-1-propyl)-3-hydroxybutanoate as an oil.

Workup

  1. customthe mixture is evacuated
  2. custompurged with nitrogen
  3. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-8cc133c90161457289856374ac980202
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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