반응 #89666

반응 방정식

tert-butyl 3-allyl-4-oxopyrrolidine-1-carboxylate

ammonium trifluoroacetate

2-nitrophenyl isocyanide

2,2,2-trifluoroethanol

→

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

수율 51.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타was placed in a 60° C.
2. 2
   세척washed with water (3×20 mL)
3. 3
   추출the combined aqueous phase was re-extracted with ethyl acetate (20 mL)
4. 4
   세척The combined organic phase was washed with saturated aqueous sodium chloride (20 mL)
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by silica gel chromatography (90 g column, 0-5% ethyl acetate in methylene chloride)

실험 절차

While under nitrogen, a stirred mixture of tert-butyl 3-allyl-4-oxopyrrolidine-1-carboxylate (600 mg, 2.66 mmol), ammonium trifluoroacetate (698 mg, 5.33 mmol) and 2-nitrophenyl isocyanide (690 mg, 4.6 mmol) in 2,2,2-trifluoroethanol (2.7 mL) was placed in a 60° C. oil bath and stirred overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate (40 mL), washed with water (3×20 mL) and the combined aqueous phase was re-extracted with ethyl acetate (20 mL). The combined organic phase was washed with saturated aqueous sodium chloride (20 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by silica gel chromatography (90 g column, 0-5% ethyl acetate in methylene chloride) gave tert-butyl 4-allyl-3-[(2-nitrophenyl)carbamoyl]-3-[(trifluoroacetyl)amino]-pyrrolidine-1-carboxylate (665 mg, 51%, 3:2 mixture of diastereomers) as an amber gum. LC-MS ESI+ MS found for C21H25F3N4O6 m/z 509.0 (M+Na). LC-MS ESI−MS found for C21H25F3N4O6 m/z 485.1 (M−H).

출처