Synthesis
At room temperature, TEA (30.4 g, 300.0 mmol) was added dropwise to a mixed solution of nortropinone hydrochloride (16.2 g, 100.0 mmol) and DCM (300 mL), while maintaining the system temperature below 30 °C. After the addition was complete, (Boc)₂O (24.0 g, 110.0 mmol) was added in portions to the reaction system. The reaction system was then stirred at room temperature for 6 h. TLC showed that the reaction of the starting materials was complete. The reaction solution was washed once with 1 M dilute hydrochloric acid, saturated Na₂CO₃ aqueous solution, and saturated brine. The organic phase was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure to give 22.1 g (yield: 98%) of the target compound as a colorless oil.
Chemical Properties
Off-White Solid
Uses
N-Boc-Nortropinone is a 8-azabicyclo[3.2.1]octane derivative useful as opioid receptor modulator.
Definition
N-Boc-Nortropinone can be used for the preparation of Tropine derivatives. Tropine and its derivatives are a class of important heterocyclic compounds, which are alkaloids present in natural plants. Due to their diverse biological activities, they are widely used in the fields of pesticides, pharmaceuticals, and chemical industries. N-Boc-Nortropinone can also be used to synthesize a new bicyclic vinyl boronate[1].
References
[1] Shyamali Ghosh. “Convenient preparation of aryl-substituted nortropanes by SuzukiMiyaura methodology.” Canadian Journal of Chemistry 29 1 (2006): 555–560.
