Potassium Iodide → 1-(Methylcarbonyloxy-methyl)-5-(cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one
Reaktionsgleichung
Br[CH2:2][CH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OC[CH2:16][N:17]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:18]1=[O:31])=O.[C:32](=[O:35])([O-])[O-:33].[K+].[K+].[I-].[K+].[C:40](#N)C>>[CH3:40][C:32]([O:33][CH2:16][N:17]1[C:30]2[C:25](=[CH:26][C:27]([CH2:2][CH:3]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:28][CH:29]=2)[C:19]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[C:18]1=[O:31])=[O:35]Komponenten
6
Edukt 5
Produkt 1
Reaktionsbedingungen
- Temperatur
- 45 °C
Versuchsvorschrift
1-Bromomethyl-cyclooctane (0.026 g, 0.216 mmol) and 1-(methylcarbonyloxy-ethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.029 g, 0.105 mmol) were dissolved in acetonitrile (1.5 mL). Potassium carbonate (0.044 g, 0.316 mmol) and a catalytic amount of potassium iodide were added and the reaction mixture was stirred at 45° C. under nitrogen atmosphere for 18 hours. The reaction mixture was then partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (3% methanol/dichloromethane) to yield the title compound as an oil.
Aufarbeitung
- customThe reaction mixture was then partitioned with water and ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried with Na2SO4
- filtrationfiltered
- customthe solvent evaporated in vacuo
- customto yield a crude oil
- customThe crude oil was purified via flash chromatography (3% methanol/dichloromethane)
Quellen und Nachweise
- ORD-Eintrag
- ord-839936d770ef41f1a7c8425a6ccf07e9
- Quelldatensatz
- uspto-grants-2010_02
- Patentnummer
- US07655670B2
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