Oxygen → 3-Benzo[1,3]dioxol-5-yl-2-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

HRID 2415355Notes

Reaction equation

HRID 2415355 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5C(=[CH:16][CH:17]=[CH:18][CH:19]=5)C=4C[CH2:12][N:11]3[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:4][C:3]=2[O:2]1.C[C:31]([CH3:34])([O-:33])[CH3:32].[K+].O=O>CN(C=O)C>[CH2:23]([N:11]1[CH2:12][C:34]2[C:31](=[O:33])[C:32]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[NH:21][C:22]=2[CH:10]1[C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 129930141-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 129930153-Benzo[1,3]dioxol-5-yl-2-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3,4-Methylenedioxyphenyl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline (0.79 g, 2.0 mmol) (prepared as in Example 1) was dissolved in dry DMF (15 mL). Potassium t-butoxide (0.56 g, 5.0 mmol) was added, followed by oxygen, bubbled in via syringe needle. The mixture was maintained at room temperature for one hour and then poured onto a mixture of 1N HCl (5 mL), water (35 mL) and ethyl acetate (35 mL). A fluffy yellow precipitate was collected, the organic layer removed, and the aqueous solution extracted with ethyl acetate (15 mL). The extracted layer was agitated and set aside overnight. The following day an additional quantity of product (as a precipitate) was collected. Drying of the combined solids yielded the product as a yellow powder.

Workup

  1. custombubbled in via syringe needle
  2. additionpoured onto a mixture of 1N HCl (5 mL), water (35 mL) and ethyl acetate (35 mL)
  3. customA fluffy yellow precipitate was collected
  4. customthe organic layer removed
  5. extractionthe aqueous solution extracted with ethyl acetate (15 mL)
  6. customThe following day an additional quantity of product (as a precipitate) was collected
  7. customDrying of the combined solids

Sources & evidence

ORD record
ord-7a0d580d01c442bc8241e13ebc2bea10
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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