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

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Reaction Steps

1.55 ml (1l mmol) of diisopropylamine is dissolved in 20 ml of absolute THF under argon and 7.75 ml 10 (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 2.6l g (10 mmol) of (4S)-3-(3-phenylpropionyl)-4-(2-propyl)-oxazolidin-2-one (J. J. Plattner et al., J. Med. Chem. 1988, 3l (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.

Provenance & Evidence