Tetrahydrofuran → HCID 10976223, compound

Participants

Reaction Steps

To a 0° C. solution of 4(S)-isobutyl-5(S)-vinyl-2-oxazolidinone (4.7 g, 0.028 mole) in THF (20 mL) was added 9-BBN [9-borabicyclo(3.3.1)nonane, 75 mL, 0.0375 mole in THE] by dropwise addition. After stirring for 5 hours at room temperature, the reaction was quenched by the addition of water (1 mL). A solution of NaOH (6.7 g) in water (21 mL) was then added followed by careful addition of H2O2 (18 mL of 30%). The resulting mixture was heated at 65° C. for 1 hour, the THF was partially evaporated and the residue was distributed between ethyl acetate and brine solution. The organic phase was washed with brine solution and dried over MgSO4. Evaporation of the solvent gave a residual oil which was flash chromatographed on silica get eluting with 5% MeOH in methylene chloride. The pure fractions were combined and evaporated to give 4.62 g of 4(S)-isobutyl-5(S)-(2-hydroxyethyl)-2-oxazolidinone. A solution of this material (3.95 g, 0.021 mol) and triethylamine (3.2 g, 0.032 mol) in methylene chloride (40 mL) was cooled to 0° C. and treated by dropwise addition with mesyl chloride (2.89 g, 0.025 mol). After stirring for 1 hour at 0-5° C., the methylene chloride was washed successively with 0.5 N HCl, aqueous NaHCO3 and brine solution. The organic solution was dried and evaporated to a solid product. Recrystallization from hexane/methylene chloride gave 3.9 g (70%) of product, m.p. 99°-100° C.

Provenance & Evidence