Tetrahydrofuran → (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone

1.57M n-butyllithium hexane solution (96 ml, 150 mmol) was slowly added dropwise to a THF (400 ml) solution of (R)-4-benzyl-2-oxazolidinone (25.36 g, 143 mmol) at −78° C. under stirring. Subsequently propionyl chloride (13.7 ml, 157 mmol) was added at once and the reaction solution was stirred at the same temperature for 30 minutes. After the reaction solution was warmed to room temperature for 30 minutes, it was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; heptane:ethyl acetate=5:1) to obtain the title compound (36.58 g) as a white solid.

1. stirringwas stirred at the same temperature for 30 minutes
2. washwashed with water and brine
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. filtrationAfter the drying agent was filtered off
5. concentrationthe organic layer was concentrated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; heptane:ethyl acetate=5:1)

ORD record

ord-e5a51c702b2440f9805855489bdfbc6a

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816401B2