反应详情

To a solution of t-butyl 4-bromomethyl-3-nitrobenzoate (2.27 g, 7.2 mmol) (Int. J. Peptide Res., 36, 31 (1990)) in DMF (25 mL) was added a suspension of potassium t-butyl methyl iminodicarboxylate (J.C.S. Perkin I, 1088, (1977)) (1.56 g, 7.3 mmol) in DMF (20 mL). The dark brown solution was stirred 1 h and poured into water and extracted with ethyl acetate. The combined organic layers were washed with water, dried (sodium sulfate) and concentrated to give a pale orange oil which was purified by flash chromatography (silica gel, 20% ethyl acetate/hexane) to give the title compound (2.15 g, 73%). 1H NMR (400 MHz, CDCl3) δ8.65 (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).

1. extractionextracted with ethyl acetate
2. washThe combined organic layers were washed with water
3. dry with materialdried (sodium sulfate)
4. concentrationconcentrated
5. customto give a pale orange oil which
6. customwas purified by flash chromatography (silica gel, 20% ethyl acetate/hexane)