Reaktion #89666

Reaktionsgleichung

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

Ausbeute 51.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed in a 60° C.
2. 2
   Waschenwashed with water (3×20 mL)
3. 3
   Extraktionthe combined aqueous phase was re-extracted with ethyl acetate (20 mL)
4. 4
   WaschenThe combined organic phase was washed with saturated aqueous sodium chloride (20 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigePurification by silica gel chromatography (90 g column, 0-5% ethyl acetate in methylene chloride)

Vorschrift

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).

Quelle