Reaktion #171167

Reaktionsgleichung

1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine]

diisopropylethylamine

4-chloro-cinnamyl chloride

→

1-methanesulfonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine]

Ausbeute 45.8%

Lösungsmittel

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water, brine
2. 2
   Trocknendried (Na2SO4)
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe residue was purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)

Vorschrift

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+).

Quelle