HCID 67802217, compound → HCID 67802081, compound

HRID 1900829Notes

Reaction equation

HRID 1900829 reaction equation
[NH2:1][CH2:2][CH:3]1[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3.[ClH:20].[H][H]>O.[Pd]>[NH2:1][CH2:2][CH:3]1[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[CH:9]([CH3:17])[CH2:8]3.[ClH:20]

Participants

5

Reactant 2

HCID 67802217HCID 67802217, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67802081HCID 67802081, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The trans compound obtained in Example 297 (380 mg, 1.29 mmol) was dissolved in water (30 ml). To the solution, 10% palladium-on-carbon (400 mg) was added. The mixture was stirred at 80° C. for 2 days in the stream of hydrogen. After removing the catalyst by filtration, the filtrate was distilled off under reduced pressure, and the residue was subjected to recrystallization from methanol-ether to obtain 227 mg of the title compound in a trans form as colorless crystals (59%). By a similar procedure using the cis compound obtained in Example 297 (165 mg, 0.56 mmol), 85 mg of the title compound in a cis form was obtained as colorless crystals (51%).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. distillationthe filtrate was distilled off under reduced pressure
  4. customthe residue was subjected to recrystallization from methanol-ether

Sources & evidence

ORD record
ord-6d601b99d1264f0b8e742b269a2a464b
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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