3-tert-butyl 2-diphenylmethyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate → (2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid

HRID 2287494

Reaction equation

HRID 2287494 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([O:9]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:8])[CH:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:3]1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[C:26]([O:25][C:23]([CH:4]1[CH2:3][C:2](=[O:1])[O:6][CH:5]1[C:7]([OH:9])=[O:8])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 538073673-tert-butyl 2-diphenylmethyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidYield 76.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

148 mg of 3-tert-butyl 2-diphenylmethyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate in 4 ml of ethyl acetate was catalytically reduced with 15 mg of a 10% palladium-carbon catalyst at room temperature at atmospheric pressure of hydrogen for 15 hours. The catalyst was filtered off, and the solvent was evaporated in vacuo. The residue was washed with benzene to give 66 mg of the title compound as a white crystalline powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated in vacuo
  3. washThe residue was washed with benzene

Sources & evidence

ORD record
ord-6c243f1fbe8146a8b3bbede3a45e2142
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Linked notes

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