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

HRID 1431934Notes

Reaction equation

HRID 1431934 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]>CCOC(C)=O.[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 B-2 (2.5 g) in EtOAc (50 mL) is added 10% Pd/C (0.25 g) and the reaction stirred under a hydrogen atmosphere for 20 hours. The suspension is filtered through Celite, washed with EtOAc (3×) and then concentrated in vacuo to afford (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester B-3.

Workup

  1. filtrationThe suspension is filtered through Celite
  2. washwashed with EtOAc (3×)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6677eb734b14ac8a3076bcfe4b8dc1b
Source dataset
uspto-grants-2009_11
Patent number
US07612059B2

Reaction notes

Loading…