(N-Acetyl)-(4R)-benzyl-2-oxazolidinone → 4-Benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-acetyl-4-benzyl-oxazolidin-2-one (2.1 g, 9.4 mmol) in THF (40 mL) was stirred under N2 at −78° C. Lithium diisopropyl amine (5.2 mL, 10.3 mmol, 2.0 M in heptane/THF/ethylbenzene) was then added dropwise. The mixture was stirred for 20 min. 1-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene (3.2 g, 9.4 mmol) dissolved in 20 mL THF was cannulated over and the mixture was stirred for 2 h at −78° C. After quenching the reaction sat. NH4Cl, the mixture was warmed to r.t., extracted with CH3Cl, washed with water and brine, dried and concentrated. Filtration of the solids with 1:1 hexane/EtOAc, afforded 4 g of white solids. Yield: 75%.

Provenance & Evidence