Reaktion #5462

Reaktionsgleichung

water

sodium hydroxide

water

1-azabicyclo[3.3.1]nonane-5-carboxamide

lithium aluminum hydride tetrahydrofuran

→

colorless oil

Ausbeute 77.0%

1-Azabicyclo[3.3.1]nonane-5-methanamine

Ausbeute 77.0%

Lösungsmittel

Ether

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 4 hours
2. 2
   Filtrationthe mixture was filtered through Celite
3. 3
   Waschenthe filter cake was washed with ether
4. 4
   EinengenThe filtrate was concentrated in vacuo

Vorschrift

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.

Quelle