Triethyl phosphite → HCID 57758671, compound

To a solution of tert-butyl(3R)-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (9.90 g, 32.6 mmol) and tri ethyl phosphite (6.71 mL, 39.1 mmol) in anhydrous tetrahydrofuran (165 mL), lithium bistrimethylsilyl amide (45.7 mL, 45.7 mmol, 1.0M solution in tetrahydrofuran) was added at −5° C., and the mixture was stirred at the same temperature for 30 minutes. After bubbling oxygen gas into the reaction mixture for 30 minutes, saturated aqueous solution of ammonium chloride (150 mL) was added in an ice bath, and the mixture was concentrated under reduced pressure. Water (100 mL) was added to the residue and the mixture was extracted with ethyl acetate (200 mL×2). The organic layer was washed with saturated aqueous solution of sodium chloride (200 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane ethyl acetate, 1:1→1:4) to obtain 7.73 g (74%) of the title compound as a pale yellow oily substance.

1. customAfter bubbling oxygen gas into the reaction mixture for 30 minutes
2. additionsaturated aqueous solution of ammonium chloride (150 mL) was added in an ice bath
3. concentrationthe mixture was concentrated under reduced pressure
4. additionWater (100 mL) was added to the residue
5. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
6. washThe organic layer was washed with saturated aqueous solution of sodium chloride (200 mL)
7. dry with materialdried with anhydrous sodium sulfate
8. filtrationAfter the filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. customthe residue was purified by silica gel column chromatography (hexane ethyl acetate, 1:1→1:4)

ORD record

ord-99f07a3018e24e819b267ea37eb8afe4

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563805B2