反応 #328745

反応方程式

acetic anhydride

tert-butyl 3-oxopyrrolidine-1-carboxylate

sodium bis(trimethylsilyl)amide

→

desired product

tert-Butyl 3-acetyl-4-oxopyrrolidine-1-carboxylate

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGstirred at room temperature for 20 min
2. 2
   その他The reaction mixture was quenched by the dropwise addition of water
3. 3
   濃縮concentrated under vacuum
4. 4
   workup.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. 5
   その他The aqueous layer was separated
6. 6
   workup.ADDITIONacidified by careful addition of hydrochloric acid to pH 3
7. 7
   抽出extracted with ethyl acetate (75 mL)
8. 8
   洗浄The organic layer was washed with brine
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    ろ過filtered
11. 11
    その他evaporated

実験手順

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.

出典