Hydrogen Peroxide → HCID 57546233, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)allyloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (84 mg, 0.133 mmol) in tetrahydrofuran (2 mL, 0.133 mmol) at 0 C was added Borane-THF (0.267 mL, 0.267 mmol). The reaction was allowed to slowly warm to room temperature over 1.5 h. The reaction was recooled to 0 C and treated with hydrogen peroxide (30%) (1.3 mL, 0.133 mmol) followed by sodium hydroxide (0.6 mL, 2.400 mmol). After stirring for 30 min, the reaction was diluted with ether and quenched by addition of sat'd ammonium chloride. The mixture was extracted with ether, washed with brine, dried over magnesium sulfate, filtered and concentrated. It was purified by column chromatography (30% to 47% EtOAc/Hex) to give title compound (61 mg, 0.094 mmol, 70.6% yield) as white foam solid. 1H-NMR (CDCl3, 500 MHz) δ 8.02 (s, 1H), 7.52 (d, J=1.5 Hz, 1H), 7.30 (m, 2H), 7.06 (t, J=8.8 Hz, 2H), 6.70 (bs, 1H), 5.64 (AB, Δν=17.1 Hz, J=10.7 Hz, 2H), 5.07 (t, J=6.7 Hz, 1H), 3.75 (m, 2H), 3.57 (m 2H), 3.38 (m, 2H), 2.95-3.25 (m, 2H), 2.05-2.25 (m, 2H), 1.85 (m, 2H), 1.43 (s, 9H), 0.90 (t, J=8.5 Hz, 2H), −0.06 (s, 9H). LC/MS (HPLC method 3): tR=4.29 min, 648.2(MH)+.

Provenance & Evidence