反应详情

Anhydrous methylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min. A solution of t-butyl 4-bromomethyl-3-nitrobenzoate (5.0 g, 15.8 mmol) (Int. J. Peptide. Res., 36, 31 (1990)) in DMF (10 mL) was added dropwise to the cold amine solution. The solution was stirred at 0° for 30 min and poured into water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water, dried (sodium sulfate) and concentrated to give a yellow-brown oil. The oil was purified by chromatography (silica gel, 3% isopropanol/CH2Cl2) to give the title compound (1.5 g, 36%). 1H NMR (400 MHz, CDCl3) δ8.5 (s, 1H), 8.2 (d, 1H), 7.7 (d, 1H), 4.05 (s, 2H), 2.5 (s, 3H), 1.6 (s, 9H).

1. customAnhydrous methylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min
2. extractionThe mixture was extracted with ethyl acetate
3. washthe combined organic layers were washed with water
4. dry with materialdried (sodium sulfate)
5. concentrationconcentrated
6. customto give a yellow-brown oil
7. customThe oil was purified by chromatography (silica gel, 3% isopropanol/CH2Cl2)