Potassium Carbonate → HCID 69414322, compound

HRID 585808Notes

Reaction equation

HRID 585808 reaction equation
[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][NH:13][CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][O:19][C:17](=[O:18])[CH2:16][N:13]1[CH2:12][CH2:11][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[C:3]=3[CH2:4][C@@H:5]2[CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 69415545HCID 69415545, compound

Product 1

HCID 69414322HCID 69414322, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(10aR)-9-Bromo-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (0.07 g, 0.27 mmol) and methyl bromoacetate (43 mg, 0.27 mmol) were dissolved in acetonitrile (2 mL). Potassium carbonate (44 mg, 0.32 mmol) was added and the solution was boiled with stirring for 15 h. The solvent was removed and the residue was partitioned between dichloromethane and brine. Organic phases were pooled, dried with MgSO4 and the solvent was evaporated. Chromatography on silica gel (dichloromethane/methanol 98:2) gave (10aR)-(9-bromo-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indol-2-yl)-acetic acid methyl ester (57 mg, 63%), MS: m/e=325.2 (M+H+).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between dichloromethane and brine
  3. dry with materialdried with MgSO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5d85252190364059aa09ad14f13bff99
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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