反応 #89666

反応方程式

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

収率 51.0%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   その他was placed in a 60° C.
2. 2
   洗浄washed with water (3×20 mL)
3. 3
   抽出the combined aqueous phase was re-extracted with ethyl acetate (20 mL)
4. 4
   洗浄The combined organic phase was washed with saturated aqueous sodium chloride (20 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by silica gel chromatography (90 g column, 0-5% ethyl acetate in methylene chloride)

実験手順

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).

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