Reacción #5462

Ecuación de reacción

water

sodium hydroxide

water

1-azabicyclo[3.3.1]nonane-5-carboxamide

lithium aluminum hydride tetrahydrofuran

→

colorless oil

Rendimiento 77.0%

1-Azabicyclo[3.3.1]nonane-5-methanamine

Rendimiento 77.0%

Disolventes

Ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 4 hours
2. 2
   Filtraciónthe mixture was filtered through Celite
3. 3
   Lavadothe filter cake was washed with ether
4. 4
   ConcentraciónThe filtrate was concentrated in vacuo

Procedimiento

A suspension of 1-azabicyclo[3.3.1]nonane-5-carboxamide (1.80 g, 10.7 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was treated (via syringe) with 1.0N lithium aluminum hydride/tetrahydrofuran (25 mL, 25 mmol), and the mixture was refluxed for 4 hours and cooled (0° C.). The mixture was treated carefully dropwise sequentially with water (1 mL), 15% sodium hydroxide (1 mL), and water (3 mL). Ether (50 mL) was added, the mixture was filtered through Celite, and the filter cake was washed with ether. The filtrate was concentrated in vacuo to afford 1.27 g (77%) of colorless oil.

Fuente