(R)-4-Benzyl-2-oxazolidinone → (R)-3-((E)-8-methylnon-6-enoyl)-4-benzyloxazolidin-2-one

Temperature

-78 °C

To a cooled (−78° C.) solution of (R)-4-benzyloxazolidin-2-one (2.817 g, 15.899 mmol) in 40 mL of THF, was added n-BuLi (6.4 mL, 15.899 mmol, 2.5 M in hexane). The resulting mixture was stirred at −78° C. under N2 for 15 min. and then (E)-8-methylnon-6-enoyl chloride (3.000 g, 15.899 mmol) was added. After stirring at −78° C. for 1 h and then being warmed to room temperature under N2 for overnight, the reaction mixture was quenched with 80 mL of NH4Cl solution and extracted with dichloromethane (60 mL×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (4.468 g, 85% yield). GC-MS: tR=6.2 min; m/z 329 (M+).

1. stirringAfter stirring at −78° C. for 1 h
2. temperaturebeing warmed to room temperature under N2 for overnight
3. customthe reaction mixture was quenched with 80 mL of NH4Cl solution
4. extractionextracted with dichloromethane (60 mL×3)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe product was isolated by Flash column chromatography (silica gel column)
9. washeluting with 0-30% ethyl acetate/hexanes

ORD record

ord-43be0c465c7e434da20269c201688535

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807720B2