반응 #89667

반응 방정식

tert-butyl 4-allyl-3-[(2-nitrophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate

ammonium chloride

→

tert-butyl 4-allyl-3-[(2-aminophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate

수율 99.1%

용매

ethyl acetate

methanol

반응 조건

후처리

1. 1
   여과filtered through a pad of Celite
2. 2
   세척The pad was washed with ethyl acetate
3. 3
   농축the filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONThe residue was re-diluted with ethyl acetate (25 mL) and water (20 mL)
5. 5
   기타the layers were separated
6. 6
   세척The organic phase was washed with water (10 mL) and saturated aqueous sodium chloride (10 mL)
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated
9. 9
   기타dried under high vacuum for ˜2 h

실험 절차

A solution of tert-butyl 4-allyl-3-[(2-nitrophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate (0.816 g, 1.68 mmol) in methanol (30 mL) was treated with ammonium chloride (0.897 g, 16.8 mmol) and zinc (2.19 g, 33.5 mmol). After stirring at room temperature for 40 min, the mixture was diluted with ethyl acetate (30 mL) and filtered through a pad of Celite. The pad was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was re-diluted with ethyl acetate (25 mL) and water (20 mL), and the layers were separated. The organic phase was washed with water (10 mL) and saturated aqueous sodium chloride (10 mL), dried over Na2SO4 and concentrated and dried under high vacuum for ˜2 h to give the tert-butyl 4-allyl-3-[(2-aminophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate intermediate (760 mg, 3:2 mixture of diastereomers) as a off-white foam that was used without further purification.

출처