1-Azabicyclo[3.2.2]nonan-4-one → HCID 68328094, compound

Temperature

0 °C

To 1-azabicyclo[3.2.2]nonan-4-one (0.20 g, 1.4 mmol) in 1,4-dioxane (2.8 mL) at 0° C. was added lithium aluminum hydride [1.0M/THF] (1.7 mL, 1.7 mmol). The reaction mixture was maintained at 0° C. for 15 minutes. The reaction was quenched by the stepwise addition of 46 □L of H2O, 46 □L of 15% aqueous NaOH, and 138 □L of H2O. The mixture was filtered through Celite which was subsequently washed with EtOAc. The solvent was removed in vacuo to afford the product (0.19 g, 96%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.90-3.86 (m, 1H), 3.09-3.03 (m, 1H), 2.96-2.91 (dd, J=9.2, 6.8 Hz, 1H), 2.86-2.75 (m, 3H), 2.71-2.64 (m, 1H), 2.34-2.27 (bs s, 1H), 1.98-1.86 (m, 3H), 1.71-1.59 (m, 3H), 1.51-1.35 (m, 1H) ppm.

1. customThe reaction was quenched by the stepwise addition of 46 □L of H2O, 46 □L of 15% aqueous NaOH, and 138 □L of H2O
2. filtrationThe mixture was filtered through Celite which
3. washwas subsequently washed with EtOAc
4. customThe solvent was removed in vacuo

ORD record

ord-fa98d0b3e79e42cda7383bedbf015e07

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139580B2