Methanol → HCID 18713369, compound

Participants

Reaction Steps

n-Butyl lithium (4.6 ml. of 1.6 M solution in THF, 7.36 mM) was added to a stirred solution of t-butanol (0.505 g) in dry THF at −20° C. under nitrogen and the mixture stirred for 20 minutes. The temperature was lowered to −60° C. and 2-(4-ethoxycarbonylaminobenzoyl)-1-(2-trimethylsilylethoxymethyl)pyrrole (2.2 g. 5.67 mM) added over 15 minutes. The mixture was stirred for 50 minutes and a solution of R-(−) glycidyl butyrate (0.9 g. 6.25 mM) in dry THF (5 ml) added. The mixture was allowed to warm to ambient temperature and stirred for 24 hours. MeOH (20 ml) was added and the solution evaporated and the residue partitioned between EtOAc and water The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using 2% MeOH/dichloromethane as eluant, to give 5(R)-hydroxymethyl-N-(4-[1-(2-trimethylsilylethoxymethyl)pyrrol-2-ylcarbonyl]phenyl)oxazolidin-2-one as an oil (0.77 g; MS: 417 (MM−)).

Provenance & Evidence