Acetic Acid → 1,2,3,4-Tetrahydro-2-(tert-butoxycarbonyl)-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one
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]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:4][C:3]=2[O:2]1.CC(C)([O-:33])C.[K+].O=O.C(O)(=O)C>CN(C=O)C.O.C(OCC)C>[C:26]([O:25][C:23]([N:11]1[CH2:12][C:13]2[C:14](=[O:33])[C:15]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)=[O:24])([CH3:28])([CH3:27])[CH3:29]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
2-t-Butoxycarbonyl-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (4.09 g, 10.4 mmol) (prepared as in Example 9) was dissolved in dry DMF (100 mL). Potassium t-butoxide (2.55 g, 22.7 mmol) was introduced in one portion and the suspension was stirred until a clear solution was obtained. Oxygen gas was then passed through the solution via a syringe needle for 16 h. The reaction was quenched by the addition of glacial acetic acid (25 mmol) and poured into a mixture of diethyl ether and water, which resulted in a precipitate that was collected by filtration. The product was purified by flash chromatography (0-10% MeOH/CHCl3) to yield the product as a white solid.
Workup
- customwas obtained
- customresulted in a precipitate that
- filtrationwas collected by filtration
- customThe product was purified by flash chromatography (0-10% MeOH/CHCl3)
Sources & evidence
- ORD record
- ord-391d69950a0f4e56bb08975e80418756
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818646B2
Reaction notes
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