HCID 86613496, compound → HCID 23147612, compound

HRID 495282Notes

Reaction equation

HRID 495282 reaction equation
[CH:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])=O>CO.[C].[Pd]>[OH:10][C:6]1[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:3]([CH3:1])=[C:8]([OH:9])[CH:7]=1

Participants

4

Reactant 1

HCID 86613496HCID 86613496, compound

Product 1

HCID 23147612HCID 23147612, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Compound 55 (44 mg, 0.15 mmol) obtained in Example 55 was dissolved in methanol (10 mL), and 10% palladium-carbon (50% wet., 40 mg) was added thereto and stirred under hydrogen pressure (0.3 MPa) at room temperature for 8 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure, purified through preparative thin-layer chromatography (methanol/chloroform 1/9) and crystallized (ethyl acetate/n-hexane=1/4) to obtain Compound 56 (31 mg, 74%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. custompurified through preparative thin-layer chromatography (methanol/chloroform 1/9)
  4. customcrystallized (ethyl acetate/n-hexane=1/4)

Sources & evidence

ORD record
ord-7bbbcdf392dd496884c9017a7e898361
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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