HCID 57228780, compound → HCID 18641659, compound

HRID 1089029Notes

Reaction equation

HRID 1089029 reaction equation
C([NH:11][C@H:12]1[C@H:23]2[C:24]3[C:15](=[CH:16][C:17]([O:33][CH3:34])=[C:18]([O:31][CH3:32])[C:19]=3[CH2:20][C@@H:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:22]2)[CH2:14][CH2:13]1)(OCC1C=CC=CC=1)=O.[H][H]>CO.[Pd]>[NH2:11][C@H:12]1[C@H:23]2[C:24]3[C:15](=[CH:16][C:17]([O:33][CH3:34])=[C:18]([O:31][CH3:32])[C:19]=3[CH2:20][C@@H:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:22]2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 57228780HCID 57228780, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18641659HCID 18641659, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 0.65 g (1.4 mmol) of [1R,8S,9aR]-1-carbobenzyloxyamino-5,6-dimethoxy-2,3,7,8,9,9a-hexahydro-8-phenyl-phenalene, from Step 6, in 50 mL of methanol and 0.1 g of 10% palladium on carbon was stirred under 1 atmosphere of hydrogen for 1 hour. The solid dissolved as the reaction proceeded. The palladium catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give 0.4 g (87% yield) of crude product which was carried on to the next step without further purification.

Workup

  1. dissolutionThe solid dissolved as the reaction
  2. customThe palladium catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f43e9ef8920c4214b58aa87a8232aab2
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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