反应详情

温度

0 °C

To a solution of (2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine (1000 mg, 2.46 mmol) in dry tetrahydrofuran (10 mL) under an atmosphere of nitrogen, n-butyllithium (1.6M, 2.3 mL, 3.69 mmol) was added over 5 min at −70° C. The reaction mixture was stirred at 0° C. for 10 min before triethyl borate (0.50 mL, 2.95 mmol) was added. The reaction mixture was stirred for additional 5 min at 0° C. and then allowed to reach ambient temperature and stirred for another 2 h. The reaction mixture was quenched with saturated ammonium chloride (aq) and a white precipitate was filtered off. The filtrate was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate and concentrated in vacuo to yield 612 mg (67%) of the title compound as a solid: 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (d, 1 H), 7.39-7.45 (m, 4 H), 7.28-7.37 (m, 2 H), 7.02-7.26 (m, 6 H), 3.65-3.92 (m, 4 H), 3.34-3.45 (m, 1 H), 2.70-3.19 (m, 4 H), 2.16 (br. s., 1 H), 1.66-1.79 (m, 1 H); MS (ESI) m/z 371, 372[M+H+].

1. additionwas added
2. customto reach ambient temperature
3. stirringstirred for another 2 h
4. customThe reaction mixture was quenched with saturated ammonium chloride (aq)
5. filtrationa white precipitate was filtered off
6. extractionThe filtrate was extracted with ethyl acetate
7. dry with materialthe organic layer was dried over magnesium sulfate
8. concentrationconcentrated in vacuo