HCID 15200559, compound → HCID 15200565, compound

HRID 1588449Notes

Reaction equation

HRID 1588449 reaction equation
[F:1][C:2]([F:30])([CH2:27][CH2:28][CH3:29])[C:3](=[O:26])[CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([OH:12])[CH2:10][C:9](=[O:13])[C@@H:8]1[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH:23](C)C)=[O:21].[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]([F:30])([CH2:27][CH2:28][CH3:29])[C:3](=[O:26])[CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([OH:12])[CH2:10][C:9](=[O:13])[C@@H:8]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 2

HCID 15200559HCID 15200559, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15200565HCID 15200565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 15-dehydroxy-17,17-difluoro-13,14-dihydro-16-oxo-PGE2 isopropyl ester (20) (0.303 g) obtained in Example 3 in ethyl acetate (20 ml) was subjected to hydrogenation with a catalytic amount of 5% Pd-C and hydrogen gas. The reaction mixture was filtered and the filtrate was concentrated to give the crude product, which was chromatographed on a Rober column to give the titled compound (35).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas chromatographed on a Rober column

Sources & evidence

ORD record
ord-927dfc136cec4ac6b781829595180b22
Source dataset
uspto-grants-1993_06
Patent number
US05221799

Reaction notes

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