Hydrochloric Acid → HCID 56991050, compound

HRID 982125Notes

Reaction equation

HRID 982125 reaction equation
[C:1]([C@@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:24][CH3:25])=[CH:11][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:24][CH3:25])=[CH:11][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)[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67931147HCID 67931147, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 56991050HCID 56991050, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.46 g. (1.3 mmol) of [1R,8S,9aR] 1-carbomethoxy-5-methoxy-3-hydroxy-8-phenyl-7,8,9,9a-tetrahydrophenalene, from Step 3, in 50 mL of methanol, 50 mL of ethyl acetate, and 0.1 mL of concentrated hydrochloric acid is added 0.2 g of 5% palladium supported on carbon and the mixture is shaken under 4 atmospheres of hydrogen until the hydrogen uptake ceases. The catalyst is filtered through Celite filter aid and concentrated to give the title compound, which is carried on without further purification.

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. filtrationfilter aid
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b541a82cdcb4fb194405430489af95a
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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