Cesium carbonate → Ethyl 6-(2-aminoethoxy)-1-benzyl-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 82882

Reaktionsgleichung

[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH:9]1[NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][CH2:32][NH:33]C(=O)OC(C)(C)C>C(#N)C.ClCCl>[NH2:33][CH2:32][CH2:31][O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH:9]([NH:18][C:19](=[O:23])[O:20][CH2:21][CH3:22])[CH:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A suspension of ethyl 1-benzyl-6-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate (620 mg, 1.991 mmol) and caesium carbonate (1298 mg, 3.98 mmol) in acetonitrile (15 ml) was stirred at 80° C. under argon for 1 h, cooled down to 50° C. and tert-butyl 2-bromoethylcarbamate (669 mg, 2.99 mmol)dissolved in acetonitrile was slowly added. Stirred at 80° C. for 2 h. Evaporated acetonitrile, re-dissolved in dichloromethane, washed with water, co-extracted aqueous layer twice with dichloromethane and the combined organic layers were dried, filtered and evaporated and purified by flash silica gel chromatography on 40 g SiO2-cartridge using 30% ethyl acetate in cyclohexane to afford the titled compound as a brown oil. m=624 mg

Aufarbeitung

temperaturecooled down to 50° C.
additionwas slowly added
stirringStirred at 80° C. for 2 h
washwashed with water, co-extracted aqueous layer twice with dichloromethane
customthe combined organic layers were dried
filtrationfiltered
customevaporated
custompurified by flash silica gel chromatography on 40 g SiO2-cartridge

Quellen und Nachweise

ORD-Eintrag: ord-af87164024a443faa033e989b00669ec
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846743B2

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