1,4-Diazabicyclo(3.2.2)nonan-3-one → 1,4-Diazabicyclo(3.2.2)nonane

To a stirred solution of 1,4-diazabicyclo[3.2.2]nonan-3-one (1.0 g, 7.2 mmol) in 1,4-dioxane (7.2 mL) at room temperature was added lithium aluminum hydride [2.0M/THF] (4.1 mL, 8.2 mmol). The reaction mixture was then heated at reflux for 6 hours before cooling to room temperature. The reaction was quenched by the stepwise addition of 200 L of H2O, 200 L of 15% aqueous NaOH, and 600 L of H2O. The mixture was filtered through Celite which was subsequently washed with EtOAc. The combined filtrate was concentrated in vacuo to afford the product (0.82 g, 90%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.28-3.25 (m, 1H), 2.99-2.95 (m, 8H), 1.86-1.80 (m, 3H), 1.69-1.64 (m, 2H) ppm.

1. temperatureThe reaction mixture was then heated
2. temperatureat reflux for 6 hours
3. customThe reaction was quenched by the stepwise addition of 200 L of H2O, 200 L of 15% aqueous NaOH, and 600 L of H2O
4. filtrationThe mixture was filtered through Celite which
5. washwas subsequently washed with EtOAc
6. concentrationThe combined filtrate was concentrated in vacuo

ORD record

ord-9db5acc6fc684c5ba3d4f224708eddfc

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126993B2