HCID 13773202, compound → HCID 21271779, compound

HRID 247175Notes

Reaction equation

HRID 247175 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:16](=[O:25])[CH:17]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[O:19][CH:20]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]>C(O)C.[H][H].[Pd]>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][O:19][CH:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH:16]2[OH:25])=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 13773202HCID 13773202, compound

Product 1

HCID 21271779HCID 21271779, compoundYield 16.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 702EthanolSolvent

Procedure

The title product of Example 2 (840 mg, 1.96 mmole) was dissolved in 110 ml ethanol, and then hydrogenated at room temperature using 2 psi of hydrogen and 5% palladium on carbon as catalyst. Insolubles were removed by filtration and the filtrate was concentrated in vacuo, and the incompletely reduced residue (as determined by nmr in (CD3)2SO) was again hydrogenated. Purification by high performance chromatography on silica gel (using 30% by volume acetone-hexane) afforded 145 mg of the title compound as an oil. Spectral data indicate complete reduction of the pyranone moiety to the hydroxy-substituted cyclic ether.

Workup

  1. customhydrogenated at room temperature
  2. customInsolubles were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by high performance chromatography on silica gel (using 30% by volume acetone-hexane)

Sources & evidence

ORD record
ord-eaa68ee70e374288a4c2d417ba378a7b
Source dataset
uspto-grants-1987_11
Patent number
US04705871

Reaction notes

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