Reaktion #700556

Reaktionsgleichung

tert-butyl 4-bromomethyl-3-nitrobenzoate

potassium tert-butyl methyl iminodicarboxylate

water

→

title compound

Ausbeute 73.0%

tert-Butyl 4-[N-(tert-Butoxycarbonyl)-N-(methoxycarbonyl)aminomethyl]-3-nitrobenzoate

Ausbeute 73.0%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×100 mL)
2. 2
   Waschenthe combined organic layers were washed with water (5×75 mL)
3. 3
   Trocknendried (sodium sulfate)
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a pale orange oil which
6. 6
   Sonstigewas purified by flash chromatography on silica gel (20% ethyl acetate/hexane)

Vorschrift

To a solution of tert-butyl 4-bromomethyl-3-nitrobenzoate (2.27 g, 7.2 mmol) (Int. J. Peptide Res. 1990, 36, 31) in dimethylformamide (25 mL) was added a suspension of potassium tert-butyl methyl iminodicarboxylate (J.C.S. Perkin I 1977, 1088-90) (1.56 g, 7.3 mmol) in dimethylformamide (20 mL). The dark brown solution was stirred 1 h and poured into water (400 mL), extracted with ethyl acetate (3×100 mL) and the combined organic layers were washed with water (5×75 mL), dried (sodium sulfate) and concentrated to give a pale orange oil which was purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to give the title compound (2.15 g, 73%): 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.2 (d, 1H), 7.45 (d, 1H), 5.3 (s, 2H), 3.8 (s, 3H), 1.6 (s, 9H), 1.45 (s, 9H).

Quelle