Dimethylformamide → 1-(Methylcarbonyloxy-methyl)-5-(1-acenaphthyl)-spiro[indoline-3,4'-piperidin]-2-one
Reaction equation
Br[CH:2]1[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]=[CH:6][CH:5]=[C:4]3[CH2:3]1.COC([CH2:18][N:19]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]2([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:20]1=[O:33])=O.[C:34](=[O:37])([O-])[O-:35].[K+].[K+].[CH3:40]N(C)C=O>>[CH3:40][C:34]([O:35][CH2:18][N:19]1[C:32]2[C:27](=[CH:28][C:29]([CH:2]3[C:12]4=[C:13]5[C:8](=[CH:9][CH:10]=[CH:11]4)[CH:7]=[CH:6][CH:5]=[C:4]5[CH2:3]3)=[CH:30][CH:31]=2)[C:21]2([CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[C:20]1=[O:33])=[O:37]Participants
5
Procedure
1-Bromo-acenaphthene (0.022 g, 0.093 mmol) and 1-(methoxycarbonylmethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.013 g, 0.046 mmol) were dissolved in dry N,N-dimethylformamide (1 mL). Potassium carbonate (0.02 g, 0.14 mmol) was then added and the reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The reaction mixture was 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 (5% methanol/dichloromethane) to yield the title compound as a foam.
Workup
- customThe reaction mixture was 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 (5% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-b4863591d39542a7abd8812fb145e4ff
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655670B2
Reaction notes
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