Alprostadil → Dihydro-PGE1

HRID 1283486Notes

Reaction equation

HRID 1283486 reaction equation
[H][H].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:26]>[Pd].C(OCC)(=O)C>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])[CH2:9][CH2:10][C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:26]

Participants

5

Reactant 2

HCID 5280723AlprostadilHCID 178418361HCID 178418361, compound3×

Product 1

HCID 161273Dihydro-PGE1

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

R2 is methyl, R4 is hydrogen, V is --(CH2)5 --, and W is 1-pentyl. A solution of PGE1, 15-methyl ether (100 mg.) in 10 ml. of ethyl acetate is shaken with hydrogen at about 1 atmosphere pressure at 25°C. in the presence of 5% palladium on charcoal (15 mg.). One equivalent of hydrogen is absorbed in about 90 minutes. The hydrogenation is then stopped, and the catalyst is removed by filtration. The filtrate is evaporated, and the residue is chromatographed on 25 g. of silica gel, eluting with a 50-100% ethyl acetate gradient in Skellysolve B. Those fractions shown by TLC to contain the desired product free of the starting produuct and dehydration products are combined and evaporated to give the Formula-V 13,14-dihydro-PGE1 -type title compound.

Workup

  1. customthe catalyst is removed by filtration
  2. customThe filtrate is evaporated
  3. customthe residue is chromatographed on 25 g
  4. washof silica gel, eluting with a 50-100% ethyl acetate gradient in Skellysolve B
  5. customevaporated

Sources & evidence

ORD record
ord-3c3626ea2a90434c9fb4a8475f67400d
Source dataset
uspto-grants-1976_08
Patent number
US03975404

Reaction notes

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