Prostaglandin D2 → Pgd1

HRID 258641

Reaction equation

HRID 258641 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]1[C:13](=[O:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]1[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]1[C:13](=[O:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 448457Prostaglandin D22×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 5280936Pgd1

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of PGD2 (Example 16) in ethyl acetate is shaken with hydrogen at about one atmospheric pressure at ambient temperature in the presence of a 5 percent palladium-on-charcoal catalyst. Hydrogenation is stopped when one equivalent of hydrogen per equivalent of PGD2 is absorbed. Catalyst is removed by filtration and the filtrate is then concentrated under reduced pressure and the residue chromatographed on silica gel, eluting with ethyl acetate and Skellysolve B. Fractions shown to contain pure product are combined yielding the title compound.

Workup

  1. customis absorbed
  2. customCatalyst is removed by filtration
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. customthe residue chromatographed on silica gel
  5. washeluting with ethyl acetate and Skellysolve B

Sources & evidence

ORD record
ord-023356c8997c4353bb6710fd9a777a78
Source dataset
uspto-grants-1977_07
Patent number
US04033989

Linked notes

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