Levulinic Acid → 9-Methoxy-11b-methyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one

HRID 1163081

Reaction equation

HRID 1163081 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:12](=[CH:13][CH:14]=1)[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][NH:6]2.[C:15](O)(=[O:21])[CH2:16][CH2:17][C:18]([CH3:20])=O>C(OC(O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:12]([C:8]3[CH2:9][CH2:10][N:11]4[C:18]([CH3:20])([CH2:17][CH2:16][C:15]4=[O:21])[C:7]=3[NH:6]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11579Levulinic AcidHCID 176542-(2-Aminoethyl)-5-methoxyindole

Product 1

HCID 589707669-Methoxy-11b-methyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-oneYield 71.8%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A mixture of 6-methoxytryptamine (0.95 g, 5 mmol) and levulinic acid (0.7 g, 6 mmol) in ethoxyethanol is heated at ruflux temperature for 16 hours, cooled to room temperature and concentrated in vacuo to give 9-methoxy-11b-methyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one (0.97 g) identified by NMR, HPLC and MS [271.2 m/e (M+H)].

Workup

  1. temperatureis heated at ruflux temperature for 16 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1b0d087b438454ba17e4ca35b4036b7
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Linked notes

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