(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (3aR,4R,5R,6aS)-2-oxo-4-(3-oxo-4-phenoxybutyl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 561730Notes

Reaction equation

HRID 561730 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C:21](=[O:30])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1[CH2:19][CH2:20][C:21](=[O:30])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 12767308(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Product 1

HCID 22803341(3aR,4R,5R,6aS)-2-oxo-4-(3-oxo-4-phenoxybutyl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxo-4-phenoxybut-1-enyl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate, prepared in Step A, is dissolved in ethyl acetate and 10% Pd/C is added to the solution under a nitrogen atmosphere. The solution is flushed with hydrogen gas and subsequently stirred under a hydrogen atmosphere until starting material is consumed as judged by TLC. The crude reaction mixture is filtered through Celite and the solvent is removed under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes to afford the title intermediate.

Workup

  1. customThe solution is flushed with hydrogen gas
  2. customis consumed
  3. customThe crude reaction mixture
  4. filtrationis filtered through Celite
  5. customthe solvent is removed under reduced pressure
  6. customThe crude product is purified by flash chromatography on regular silica gel
  7. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-0b71dab0d80d4b7486fd74e21f3b39ee
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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