Diisopropylethylamine → 1-Methanesulfonyl-5-chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

HRID 83985

Reaktionsgleichung

Reaktionsgleichung von HRID 83985
[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]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 53728250p-Chlorocinnamyl chlorideHCID 581373391-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]

Produkt 1

HCID 689242391-Methanesulfonyl-5-chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]Ausbeute 45,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-f5ab99287f9542cdba20a7f4ba0be9a6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846907B2

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