Hydrochloric Acid → [1R*,8S*,9aR*]1-Carbomethoxy-5,6-dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene

HRID 233408Notes

Reaction equation

HRID 233408 reaction equation
[C:1]([C@@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:24][CH3:25])[C:12]=3[CH2:13][C@@H:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15]2)[C:7](O)=[CH:6]1)([O:3][CH3:4])=[O:2].Cl.[H][H]>CO.C(OCC)(=O)C.[Pd]>[C:1]([C@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:24][CH3:25])[C:12]=3[CH2:13][C@@H:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:15]2)[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 70053121HCID 70053121, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18641660[1R*,8S*,9aR*]1-Carbomethoxy-5,6-dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g (1.3 mmol) of [1 R,8 S,9a R]-1-carbomethoxy-5,6-dimethoxy-3-hydroxy-8-phenyl-7,8,9,9a-tetrahydrophenalene (182-3A) in 50 mL of methanol, 50 mL of ethyl acetate, and 0.1 mL of concentrated aqueous hydrochloric acid was solution was added 0.2 g of 5% palladium supported on carbon and the mixture was shaken under 4 atmospheres of hydrogen until the gas uptake had ceased. The palladium catalyst was removed by filtration through Celite® filter aid and the filtrate concentrated to give a white solid, which was carried on to the next step without purification.

Workup

  1. customThe palladium catalyst was removed by filtration through Celite®
  2. filtrationfilter aid
  3. concentrationthe filtrate concentrated
  4. customto give a white solid, which
  5. customwas carried on to the next step without purification

Sources & evidence

ORD record
ord-6447670b8cf04b0b89775df2655c20ca
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Reaction notes

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