Reaktion #5489

Reaktionsgleichung

Trimethylsilylmethylmagnesium chloride

Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate

→

ethyl 3-(trimethylsilylmethyl)-3-hydroxy-2-oxo-1-azacyclodecane-10-carboxylate

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux overnight
3. 3
   SonstigeThe reaction is quenched with saturated ammonium chloride
4. 4
   Extraktionextracted several times with ethyl acetate
5. 5
   TrocknenThe combined organic layers are dried (Na2SO4)
6. 6
   Sonstigethe solvent is evaporated
7. 7
   SonstigeThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Vorschrift

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.

Quelle