Sodium Hydroxide → tert-Butyl (1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-ylcarbaMate

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Reaction Steps

To a solution of the carbamate from Step A (430 mg, 1.69 mmol) in THF (2 mL) at 0° C. was added a solution of sodium hydroxide (2.0 g, 50 mmol) in water (20 mL), followed by a solution of KMnO4 (2.0 g, 12.6 mmol) in water (100 mL). The mixture was allowed to warm to room temperature and stirred overnight. Additional KMnO4 (2.0 g, 12.6 mmol) solution was added at room temperature and the mixture was stirred for additional 1 h. The mixture was extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to afford tert-butyl 9-azabicyclo[3.3.1]nonan-3-ylcarbamate (360 mg, 89%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 4.32 (br s, 1H), 3.66 (br s, 1H), 3.33-3.00 (m, 2H), 2.25-2.00 (m, 2H), 1.85-1.48 (m, 5H), 1.45 (s, 9H), 1.40-1.35 (m, 2H), 1.09-1.02 (m, 2H); MS (ESI+) m/z 241 (M+H).

Provenance & Evidence