Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate → Ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

HRID 5393

Reaktionsgleichung

[O:1]=[C:2]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3]1.[CH3:18][Si:19]([CH2:22][Mg]Cl)([CH3:21])[CH3:20]>CCOCC>[CH3:18][Si:19]([CH2:22][C:11]1([OH:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:3][C:2]1=[O:1])([CH3:21])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (5.02 g, 20.81 mmol) is dissolved in ether (50 mL), and cooled to 0° C. Trimethylsilylmethylmagnesium chloride (42.0 mL of a 1.0M solution in ether, 42.0 mmol) is added dropwise, the reaction is stirred at 0° C. for 20 minutes, and then heated to reflux overnight. The reaction is quenched with saturated ammonium chloride, and extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give separately the two diastereomers of ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate; major isomer, m.p. 129°-130° C.; minor isomer, m.p. 175°-177° C.

Aufarbeitung

temperatureheated
temperatureto reflux overnight
customThe reaction is quenched with saturated ammonium chloride
extractionextracted several times with ethyl acetate
dry with materialThe combined organic layers are dried (Na2SO4)
customthe solvent is evaporated
customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-d4fb9e46ad954be7a349fa818cd8a137
Quelldatensatz: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05244889

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