Sodium bis(2-methoxyethoxy)aluminiumhydride → 5-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

HRID 2068507

Reaktionsgleichung

CS([N:5]1[C:27]2[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=2)[C:7]2([CH2:11][CH2:10][N:9]([CH2:12]/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:8]2)[CH2:6]1)(=O)=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[Cl:28][C:24]1[CH:23]=[C:22]2[C:7]3([CH2:11][CH2:10][N:9]([CH2:12]/[CH:13]=[CH:14]/[C:15]4[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=4)[CH2:8]3)[CH2:6][NH:5][C:27]2=[CH:26][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A solution of 1-methanesulfonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] obtained in Step D (256 mg) in toluene (25 ml) under argon was treated with sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al, 65% in toluene, 0.67 ml) and the reaction mixture was stirred at 100° C. for 1 hour, cooled to room temperature, quenched by addition of ethyl acetate (10 ml), stirred for 15 min and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent ethyl acetate methanol 95:5) to afford 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (157 mg) as a yellow oil, which was characterised by its mass and NMR spectra.

Aufarbeitung

temperaturecooled to room temperature
customquenched by addition of ethyl acetate (10 ml)
stirringstirred for 15 min
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (eluent ethyl acetate methanol 95:5)

Quellen und Nachweise

ORD-Eintrag: ord-a7b12eb8ccda423fb2bcc01356a32031
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08299058B2

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