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

HRID 1089026Notes

Reaction equation

HRID 1089026 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].C(OCC)(=O)C.Cl.[H][H]>CO.[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 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 70053121HCID 70053121, compoundHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.5 g (1.3 mmol) of [1R,8S,9aR]-1-carbomethoxy 5,6 dimethoxy 3 hydroxy 8 phenyl-7,8,9,9a-tetrahydro-phenalene (54-3A), in 50 mL of methanol, 50 mL of ethyl acetate and 0.1 mL of concentrated aqueous hydrochloric acid was added 0.2 g of 5% palladium on carbon and the reaction mixture was shaken under 4 atmospheres of hydrogen until the uptake of hydrogen had ceased. The palladium catalyst was removed by filtration through Celite filter aid and the filtrate was 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 was concentrated
  4. customto give a white solid, which
  5. customwas carried on to the next step without purification

Sources & evidence

ORD record
ord-f3418961b542490b810f81205f3b39a0
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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