N-Boc-9-azabicyclo[3.3.1]nonan-3-one

Synthesis

24424-99-5

72761-60-5

512822-27-4

General procedure for the synthesis of N-Boc-9-azabicyclo[3.3.1]nonan-3-one hydrochloride from di-tert-butyl dicarbonate and 9-azabicyclo[3.3.1]nonan-3-one hydrochloride: 9-azabicyclo[3.3.1]nonan-3-one hydrochloride (12.0 g, 68.3 mmol) was suspended in tetrahydrofuran (THF, 200 mL) followed by addition of methylamine (27.6 g, 273 mmol). Di-tert-butyl dicarbonate (15.6 g, 71.7 mmol) dissolved in THF (50 mL) was added slowly and dropwise over 15 min at 15 °C. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, water was added and extracted with diethyl ether (200 mL). The organic phase was washed with water (2 x 100 mL) and subsequently purified by filtration through a short silica gel column. The final product N-Boc-9-azabicyclo[3.3.1]nonan-3-one was obtained in a yield of 15.24 g (93% yield).

References