Chlorotrimethylsilane → (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

Participants

Reaction Steps

To a mixture of (S)-4-benzyl-3-propionyloxazolidin-2-one, anhydrous MgCl2 (0.104 g, 1.09 mmol) and 3-bromobenzaldehyde in EtOAc is added Et3N followed by chlorotrimethylsilane. The reaction mixture is stirred under argon at room temperature for 24 h and then filtered through a layer of a silica gel, washing with EtOAc. The combined filtrates are concentrated under reduced pressure and the residue is purified by flash chromatography (1 to 30% EtOAc/hexane gradient) to give (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one.

Provenance & Evidence