Sodium bis(2-methoxyethoxy)aluminiumhydride → 5-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]
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]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
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-8798f0c9457348929512f941c499cc49
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08846907B2
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