Ammonium Chloride → HCID 58252526, compound

Participants

Reaction Steps

To a solution of benzyl 6-bromo-1-tert-butyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (50.4 g, 106 mmol) in tetrahydrofuran (600 mL), was added saturated aqueous ammonium chloride (600 mL) and zinc powder (20.8 g, 319 mmol). The reaction was stirred for 30 minutes at room temperature. The reaction was filtered through Celite®. The phases of the filtrate were separated and the organic phase was washed with water and saturated aqueous sodium chloride. The organics were dried over magnesium sulfate, filtered, and concentrated to provide a foam. The foam was triturated once with ethyl acetate/heptanes and once with diethylether to afford the title compound (40.4 g, 96%) as a white solid. +ESI (M+H) 396.5; 1H NMR (400 MHz, CDCl3, δ): 7.24-7.38 (m, 6H), 5.11 (s, 2 H), 3.36-3.61 (m, 4 H), 2.74 (s, 2 H), 2.54 (s, 2 H), 1.64 (s, 9 H), 1.51 (br. s., 4 H).

Provenance & Evidence