反応 #5462

反応方程式

water

sodium hydroxide

water

1-azabicyclo[3.3.1]nonane-5-carboxamide

lithium aluminum hydride tetrahydrofuran

→

colorless oil

収率 77.0%

1-Azabicyclo[3.3.1]nonane-5-methanamine

収率 77.0%

溶媒

Ether

tetrahydrofuran

反応条件

後処理

1. 1
   温度the mixture was refluxed for 4 hours
2. 2
   ろ過the mixture was filtered through Celite
3. 3
   洗浄the filter cake was washed with ether
4. 4
   濃縮The filtrate was concentrated in vacuo

実験手順

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.

出典