Reaction equation
[CH3:1][S:2]([N:5]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:7]2([CH2:11][CH2:10][NH:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[Cl:28][C:29]1[CH:38]=[CH:37][C:32]([CH:33]=[CH:34][CH2:35]Cl)=[CH:31][CH:30]=1>C(#N)C.C(OCC)(=O)C>[CH3:1][S:2]([N:5]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:7]2([CH2:11][CH2:10][N:9]([CH2:35]/[CH:34]=[CH:33]/[C:32]3[CH:37]=[CH:38][C:29]([Cl:28])=[CH:30][CH:31]=3)[CH2:8]2)[CH2:6]1)(=[O:4])=[O:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (725 mg) in acetonitrile (40 ml) were added diisopropylethylamine (0.66 ml) and 4-chloro-cinnamyl chloride (467 mg). The resulting solution was stirred at room temperature for 12 hours, diluted with ethyl acetate, washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4) to afford 1-methanesulfonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (500 mg) which was characterised by its mass and NMR spectra. MS (ES+) 437/439 (M+H+).
Workup
- washwashed with water, brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)
Sources & evidence
- ORD record
- ord-f5ab99287f9542cdba20a7f4ba0be9a6
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846907B2
Linked notes
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