HCID 18925567, compound → HCID 18925575, compound

HRID 1289146Notes

Reaction equation

HRID 1289146 reaction equation
[CH3:1][C:2]12[CH2:37][CH:5]([C:6]3([CH3:36])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16](=[O:35])[CH2:17][O:18][C:19]4[CH:34]=[CH:33][C:22]([C:23]([O:25]CC5C=CC=CC=5)=[O:24])=[CH:21][CH:20]=4)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[H][H]>O1CCOCC1.[Pd]>[CH3:1][C:2]12[CH2:37][CH:5]([C:6]3([CH3:36])[C:10]1([CH3:11])[C:9]1[CH:12]=[C:13]([C:16](=[O:35])[CH2:17][O:18][C:19]4[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:33][CH:34]=4)[CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2

Participants

5

Reactant 2

HCID 18925567HCID 18925567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18925575HCID 18925575, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

4.41 g (8.8 mmol) of the benzyl ester obtained in step (a) in 70 ml of dioxane were hydrogenated in the presence of 132 mg of palladium (10%) on charcoal at 60° C. at a hydrogen pressure of 7 bars for 8 hours. After filtration of the reaction medium through Celite and evaporation, the residue was chromatographed on silica in the eluent CH2Cl2 /ethyl ether (95:5). After the product was converted into a paste in hexane, 2.63 g (73%) of the expected compound, melting at 187.5° C., were isolated.

Workup

  1. filtrationAfter filtration of the reaction medium
  2. customthrough Celite and evaporation
  3. customthe residue was chromatographed on silica in the eluent CH2Cl2 /ethyl ether (95:5)

Sources & evidence

ORD record
ord-89a914972f7346eaa799f69d2c13924f
Source dataset
uspto-grants-1998_05
Patent number
US05747530

Reaction notes

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