HCID 383736, compound → HCID 19029819, compound

HRID 1613478Notes

Reaction equation

HRID 1613478 reaction equation
[CH3:1][C:2]1[CH:15]2[C:6]([CH3:21])([C:7]3[C:8](=[O:20])[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11](=[O:16])[C:12]=3[CH2:13][CH2:14]2)[CH2:5][CH2:4][C:3]=1[C:22]([OH:24])=[O:23]>C(OCC)(=O)C.[C].[Pd]>[OH:20][C:8]1[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11]([OH:16])=[C:12]2[C:7]=1[C:6]1([CH3:21])[CH:15]([CH2:14][CH2:13]2)[C:2]([CH3:1])=[C:3]([C:22]([OH:24])=[O:23])[CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 383736HCID 383736, compound

Product 1

HCID 19029819HCID 19029819, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

150 Milligrams of 3,4,4a,5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylic acid was dissolved in 10 ml of ethyl acetate. Thereto was added, as a catalyst, 3 ml of an ethyl acetate suspension containing 15 mg of 10% palladium-carbon. The container inside was purged with hydrogen gas, and the contents were stirred at room temperature for 3 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 135 mg of 3,4,4a,9,10,10a-hexahydro-5,8-dihydroxy-1,4a-dimethyl-7-(1-methylethyl)-2-phenanthrenecarboxylic acid.

Workup

  1. additionThereto was added, as a catalyst
  2. customThe container inside was purged with hydrogen gas
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e3fb54e9369418c8b451aae9f8e4a3c
Source dataset
uspto-grants-1993_03
Patent number
US05192817

Reaction notes

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