Acetic Anhydride → HCID 73553252, compound

To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (370 mg) in tetrahydrofuran (20 mL) at −78° C. was added sodium bis(trimethylsilyl)amide (4.18 mL, 1.0M in tetrahydrofuran). The reaction mixture was stirred for 1.5 h, then treated with acetic anhydride (0.21 mL) and stirred at room temperature for 20 min. The reaction mixture was quenched by the dropwise addition of water and concentrated under vacuum. To the basic residue, ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate solution (30 mL) with an equal volume of water were added. The aqueous layer was separated, acidified by careful addition of hydrochloric acid to pH 3 and extracted with ethyl acetate (75 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield desired product which was used in the next step without further purification.

1. stirringstirred at room temperature for 20 min
2. customThe reaction mixture was quenched by the dropwise addition of water
3. concentrationconcentrated under vacuum
4. additionTo the basic residue, ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate solution (30 mL) with an equal volume of water were added
5. customThe aqueous layer was separated
6. additionacidified by careful addition of hydrochloric acid to pH 3
7. extractionextracted with ethyl acetate (75 mL)
8. washThe organic layer was washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. customevaporated

ORD record

ord-72346807846446618a6315cc2b7bb3bb

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678905B2