Triethyl borate → [(7R)-7-(dibenzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]boronic acid

Participants

Reaction Conditions

Reaction Steps

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+].

Provenance & Evidence