3-Benzyloxycarbonyl-pentandioic acid tert-butyl ester ethyl ester → 3-Carboxy-pentanedioic acid tert-butyl ester ethyl ester

HRID 2214259Notes

Reaction equation

HRID 2214259 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]([C:15]([O:17]CC1C=CC=CC=1)=[O:16])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]([C:15]([OH:17])=[O:16])[CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 692114993-Benzyloxycarbonyl-pentandioic acid tert-butyl ester ethyl ester

Product 1

HCID 877344153-Carboxy-pentanedioic acid tert-butyl ester ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the compound of example 69 (2.29 g, 6.54 mmol) in ethanol (95%, 500 mL) was hydrogenated in the presence of a catalytic amount of palladium (10% on charcoal). After 24 h of stirring, the reaction was complete. The mixture was filtered over a celite pad and the solvent evaporated. The residue was distributed between ethyl acetate and water. The aqueous phase was extracted twice more with ethyl acetate. The recombined organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. The product was sufficiently pure on the basis of its 1H-NMR spectrum to be used in the next step. 1H-NMR(CDCl3, 400 MH: 1.23(t, J=7.1, 3H); 1.41(s, 9H); 2.53–2.81(m, 4H); 3.25(m, 1H); 4.13(m, 2H).

Workup

  1. filtrationThe mixture was filtered over a celite pad
  2. customthe solvent evaporated
  3. extractionThe aqueous phase was extracted twice more with ethyl acetate
  4. washThe recombined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-693989b6bf7b497980a05d03aee05f1a
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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