Triethylamine → 2-[3-(2,2-Dimethyl[1,3]dioxolan-4-yl)propyl]isoindole-1,3-dione
Reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:4][O:3]1.[C:12]([C:17]1[CH:27]=[CH:26][CH:25]=[C:19]2C(N[C:23](=[O:24])[C:18]=12)=O)(OCC)=[O:13].C(N(CC)CC)C>C(#N)C>[CH3:1][C:2]1([CH3:11])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][N:10]2[C:12](=[O:13])[C:17]3[C:18](=[CH:19][CH:25]=[CH:26][CH:27]=3)[C:23]2=[O:24])[CH2:4][O:3]1Participants
5
Procedure
To a stirred solution of 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)propylamine (1.05 g, 6.60 mmol) and carboethoxyphthalimide (1.45 g, 6.60 mmol) in acetonitrile (10 mL) at room temperature was added triethylamine (0.92 mL, 6.60 mmol) in one portion and the resuting mixture was stirred at room temperature for 18 hours, evaporated in vacuo and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with brine, 10% citric acid solution and brine, then dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave an oil which was purified by column chromatography on silica using ethyl acetate—petroleum ether mixture as eluent to afford a colourless oil.
Workup
- customevaporated in vacuo
- dissolutionthe residue was dissolved in ethyl acetate (50 mL)
- washThe solution was washed with brine, 10% citric acid solution and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationFiltration and concentration in vacuo
- customgave an oil which
- customwas purified by column chromatography on silica
- customto afford a colourless oil
Sources & evidence
- ORD record
- ord-600ec312e58a451ca0ee3f0d599d4ced
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259271B2
Reaction notes
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