HCID 66982554, compound → HCID 66982785, compound

HRID 516229Notes

Reaction equation

HRID 516229 reaction equation
[C:1]([C:4]1[C:5]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14][C:6]=2[CH:7]=[C:8]2[C:13]=1[NH:12][CH2:11][CH2:10][CH2:9]2)([CH3:3])=[CH2:2]>CO.[Pd]>[CH:1]([C:4]1[C:5]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14][C:6]=2[CH:7]=[C:8]2[C:13]=1[NH:12][CH2:11][CH2:10][CH2:9]2)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66982554HCID 66982554, compound

Product 1

HCID 66982785HCID 66982785, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 670 mg of t-butyl 11-isopropenyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 10 ml of MeOH was added 200 mg of palladium on carbon, followed by stirring at room temperature for 3.5 hours at normal pressure under a hydrogen atmosphere. Further, after stirring overnight at 4.5 atm under a hydrogen atmosphere, the reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 512 mg of t-butyl 11-isopropyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate.

Workup

  1. stirringFurther, after stirring overnight at 4.5 atm under a hydrogen atmosphere
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-cea02c09fbec464584ea21e658ed912a
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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