Sodium Hydroxide → tert-Butyl 4-((3-amino-5-bromobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

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tert-Butyl 4-((3-bromo-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (1.36 g, 2.69 mmol) and tin (II) chloride dihydrate (6.48 g, 28.7 mmol) were combined in ethyl acetate (20 mL) and heated at reflux for 4 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate and concentrated. The crude product was dissolved in tetrahydrofuran (10 mL), cooled to 0° C. and treated with di-tert-butyl carbonate (0.59 g, 2.69 mmol) and 10 N sodium hydroxide (0.65 mL). The reaction was allowed to warm to room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (2×), dried over sodium sulfate and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 0.25 g (19%). LC/MS (HPLC method 3): tR=2.99 min, 477.05 (MH)+.

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