반응 #328745

반응 방정식

acetic anhydride

tert-butyl 3-oxopyrrolidine-1-carboxylate

sodium bis(trimethylsilyl)amide

→

desired product

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

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at room temperature for 20 min
2. 2
   기타The reaction mixture was quenched by the dropwise addition of water
3. 3
   농축concentrated 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
   기타The aqueous layer was separated
6. 6
   workup.ADDITIONacidified by careful addition of hydrochloric acid to pH 3
7. 7
   추출extracted with ethyl acetate (75 mL)
8. 8
   세척The organic layer was washed with brine
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    기타evaporated

실험 절차

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.

출처