Potassium Carbonate → HCID 68889710, compound

HRID 853101Notes

Reaction equation

HRID 853101 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:24](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[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]([CH3:24])=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68890591HCID 68890591, compound

Product 1

HCID 68889710HCID 68889710, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.18 g (R)-8-bromo-4,7-dimethyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester in 12 ml dioxane were added 0.36 g tetrakistriphenylphosphinpalladium, 1.29 g potassium carbonate and 0.39 trimethylboroxine and the mixture was heated 1 h at reflux. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with 10% sodium bicarbonate, 10% citric acid and brine, dried over magnesium sulfate and purified by chromatography on silica gel with hexane:ethyl acetate=3:1 to yield 0.62 g (R)-4,7,8-trimethyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester as slightly yellow foam. MS: (M+H)=315.4

Workup

  1. temperaturethe mixture was heated 1 h
  2. temperatureat reflux
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with 10% sodium bicarbonate, 10% citric acid and brine
  6. dry with materialdried over magnesium sulfate
  7. custompurified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-4340c056488541aa91399bde869f47e6
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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