HCID 18925567, compound → HCID 9822717, compound

HRID 1289147Notes

Reaction equation

HRID 1289147 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]([CH:16]([OH: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 9822717HCID 9822717, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

4.41 g (8.9 mmol) of the benzyl ester obtained in Step (a) of Example 12 in 90 ml of dioxane were hydrogenated in the presence of 660 mg of palladium (10%) on charcoal at a hydrogen pressure of 7 bars at room temperature for 3 hours. After filtration of the reaction medium through Celite, evaporation and chromatography on silica in the eluent CH2Cl2 /methanol (9:1), 1.60 g (63%) of the expected compound, melting at 123.20° C., was isolated.

Workup

  1. filtrationAfter filtration of the reaction medium
  2. customthrough Celite, evaporation and chromatography on silica in the eluent CH2Cl2 /methanol (9:1), 1.60 g (63%) of the expected compound, melting at 123.20° C.
  3. customwas isolated

Sources & evidence

ORD record
ord-a4b85c55a180405c851b1d78a2748afb
Source dataset
uspto-grants-1998_05
Patent number
US05747530

Reaction notes

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