HCID 76381099, compound → HCID 13914416, compound

HRID 2118863Notes

Reaction equation

HRID 2118863 reaction equation
[C:1]([O:9][CH:10]1[CH2:18][CH:13]2[O:14][C:15](=[O:17])[CH2:16][CH:12]2[CH:11]1[CH:19]=[CH:20][CH:21]([OH:28])[CH:22]([F:27])[CH2:23][CH2:24][CH2:25][CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pt]>[C:1]([O:9][CH:10]1[CH2:18][CH:13]2[O:14][C:15](=[O:17])[CH2:16][CH:12]2[CH:11]1[CH2:19][CH2:20][CH:21]([OH:28])[CH:22]([F:27])[CH2:23][CH2:24][CH2:25][CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 76381099HCID 76381099, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13914416HCID 13914416, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To 1.1 g of platinum in 50 ml of ethyl acetate was added a solution of 11 g of (0.028 mol) of [3aR-[3a alpha,4alpha(1E,3R*,4S*),5beta,6a alpha]]-5-(benzoyloxy)-4-(4-fluoro-3-hydroxy-1-octenyl)hexahydro-2H-cyclopenta[b]furan-2-one in 110 ml of ethyl acetate. The mixture was then hydrogenated until the theoretical uptake of hydrogen was complete and then filtered through a bed of Celite. The solvent was then removed under reduced pressure and the residue chromatographed over 250 g of silica gel (toluene -.varies. 30% by volume ethyl acetate/70% by volume toluene) to afford 10.7 g of [3aR-[3a alpha,4alpha(3R*,4S*),5beta,6a alpha)]-5-(benzoyloxy)-4-(4-fluoro-3-hydroxyoctyl)hexahydro-2H-cyclopenta[b]furan-2-one (94% yield) as a colorless oil.

Workup

  1. filtrationfiltered through a bed of Celite
  2. customThe solvent was then removed under reduced pressure
  3. customthe residue chromatographed over 250 g of silica gel (toluene -.varies. 30% by volume ethyl acetate/70% by volume toluene)

Sources & evidence

ORD record
ord-49e0ae8be7924d689458f14dfea5e5fa
Source dataset
uspto-grants-1987_07
Patent number
US04680415

Reaction notes

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