HCID 68890591, compound → HCID 68890673, compound

HRID 853100Notes

Reaction equation

HRID 853100 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:22][C@@H:21]([CH3:23])[N:11]2[C:12]3[CH:13]=[C:14]([CH3:20])[C:15](Br)=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:22][C@@H:21]([CH3:23])[N:11]2[C:12]3[CH:13]=[C:14]([CH3:20])[CH:15]=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68890591HCID 68890591, compound

Product 1

HCID 68890673HCID 68890673, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

To a solution of 1.52 g (R)-8-bromo-4,7-dimethyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester in 15 ml ethanol was added 0.15 g 10% palladium on charcoal and the mixture was stirred under a hydrogen atmosphere for 6 h. A further 0.15 g 10% palladium on charcoal was added and the mixture was stirred a further 6 h under a hydrogen atmosphere. Again 0.15 g 10% palladium on charcoal was added and the mixture was stirred a further 6 h under a hydrogen atmosphere . The catalyst was removed by filtration over dicalite and the filtrate was evaporated. The residue was purified by chromatography on silica gel with hexane:ethyl acetate=4:1 to yield 0.59 g (R)-4,7-dimethyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester as a white foam. MS: (M+H)=301.3.

Workup

  1. stirringthe mixture was stirred a further 6 h under a hydrogen atmosphere
  2. stirringthe mixture was stirred a further 6 h under a hydrogen atmosphere
  3. customThe catalyst was removed by filtration over dicalite
  4. customthe filtrate was evaporated
  5. customThe residue was purified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-f0815d622f584184abaee43187e07bbf
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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