Reaktion #5037

Reaktionsgleichung

benzaldehyde

lithium diisopropylamide

(4S)-3-(3-phenylpropionyl)-4-(2-propyl)-oxazolidin-2-one

ammonium chloride

n-butyllithium

diisopropylamine

→

(4S)-3-[(2R)-2-Benzyl-(3R)-3-hydroxy-3-phenylpropionyl]-4-(2-propyl)-oxazolidin-2-one

Lösungsmittel

THF

diethyl ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred at this temperature for 10 minutes
2. 2
   workup.STIRRINGThe mixture is subsequently stirred at -70° C. for 30 minutes
3. 3
   Sonstigeto come to room temperature
4. 4
   SonstigeThe organic phase is separated off
5. 5
   Extraktionthe aqueous phase is extracted with 100 ml of diethyl ether

Vorschrift

1.55 ml (11 mmol) of diisopropylamine is dissolved in 20 ml of absolute THF under argon and 7.75 ml (12 mmol) of n-butyllithium solution (1.55M in n-hexane, Aldrich) are added at -20° C. with stirring. The mixture is stirred at this temperature for 10 minutes and the freshly prepared solution of lithium diisopropylamide prepared in this way is then added dropwise to a solution of 2.61 g (10 mmol) of (4S)-3-(3-phenylpropionyl)-4-(2-propyl)-oxazolidin-2-one (J.J. Plattner et al., J. Med. Chem. 1988, 31 (12), 2277-2288) cooled to -70° C. in 30 ml of absolute THF. The mixture is subsequently stirred at -70° C. for 30 minutes and 1.32 ml (13 mmol) of benzaldehyde are injected into the mixture via a septum. After one hour at this temperature, the mixture is hydrolyzed by adding 100 ml of saturated ammonium chloride solution and allowed to come to room temperature, and 100 ml of diethyl ether are added. The organic phase is separated off and the aqueous phase is extracted with 100 ml of diethyl ether.

Quelle