Acetic Acid → 1,2,3,4-Tetrahydro-2-(tert-butoxycarbonyl)-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]1[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-:33])C.[K+].O=O.C(O)(=O)C>CN(C=O)C.O.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:20][C:19]2[C:18](=[O:33])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]1[C:21]1[CH:26]=[CH:25][C:24]2[O:27][CH2:28][O:29][C:23]=2[CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]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-89370c90dd164e0bac7351b4771cbd01
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06635638B2
Reaction notes
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