1,3-Dimethyl-2-imidazolidinone → (2S,3S)-2-benzyl-3-hydroxy-gamma-butyrolactone

Temperature

-45 °C

Diisopropylamine (2.7 ml, 19.59 mmol) and 1.6 M of n-butyllithium-hexane solution (12.2 ml, 19.59 mmol) were added to THF (30 ml) under argon gas at 0° C. After stirring for 15 minutes, the solution was cooled to −45° C. Then, (S)-3-hydroxy-γ-butyrolactone (1 g, 9.794 mmol) in THF (20 ml) was added thereto. After stirring for 30 minutes at −45° C., benzyl bromide (1.4 ml, 11.75 mmol) and 1,3-dimethyl2-imidazolidinone (2.9 ml) in THF (20 ml) were added thereto. After stirring for 3 hours at the same temperature, an aqueous saturated ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and condensed in vacuo. The residue was purified by silica gel chromatography to give (2S,3S)-2-benzyl-3-hydroxy-γ-butyrolactone (0.577 g, yield 31%).

1. stirringAfter stirring for 30 minutes at −45° C.
2. stirringAfter stirring for 3 hours at the same temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water and saturated brine
5. dry with materialdried over magnesium sulfate, and condensed in vacuo
6. customThe residue was purified by silica gel chromatography

ORD record

ord-bb97460fad4f45e597eaf8fdb098bd39

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268515B1