diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate → Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

HRID 1710449Notes

Reaction equation

HRID 1710449 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]#[N:22])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=2)=O)C.[H][H]>CCO.O=[Pt]=O>[CH2:18]([O:17][C:15]([C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:6]3[C:4](=[O:3])[NH:22][CH2:21][CH2:20][N:7]3[C:8]=2[CH:9]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68506420Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylateYield 109.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.66 mmol) in 20 mL of absolute EtOH was added PtO2 (Adams' catalyst). The reaction mixture was hydrogenated at 50 psi of hydrogen overnight. The reaction mixture was filtered through a pad of diatomaceous earth, the solid cake was washed with dichloromethane several times. The solvent was evaporated to dryness to give 468 mg of 1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid ethyl ester as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washthe solid cake was washed with dichloromethane several times
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-3f22195600214fb980c219b22df37b03
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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