(2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester → (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester

HRID 1008279Notes

Reaction equation

HRID 1008279 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([OH:14])[C@@H:5]([CH2:10][CH:11]=[CH:12][CH3:13])[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([OH:14])[C@@H:5]([CH2:10][CH2:11][CH2:12][CH3:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 86585708(2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester

Product 1

HCID 23520166(2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To (2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester F-2 (2.5 g) in ethyl acetate (50 mL) was added 10% Pd/C (0.25 g) and the reaction stirred under a hydrogen atmosphere for 20 h. The suspension was filtered through a pad of Celite, washed with EtOAc (3×) and then concentrated in vacuo to afford (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester F-3.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. washwashed with EtOAc (3×)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d2d4959289a4b17839b824b1cb13b2a
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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