反応 #5458

反応方程式

lithium aluminum hydride tetrahydrofuran

water

sodium hydroxide

water

1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester

→

1-Azabicyclo[3.2.1]octane-5-methanol

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度refluxed for one hour
2. 2
   温度cooled (0° C.)
3. 3
   ろ過the mixture was filtered through Celite (the solid
4. 4
   洗浄was washed with tetrahydrofuran) and
5. 5
   濃縮concentrated in vacuo
6. 6
   その他to afford 6.50 g (92%) of viscous, colorless oil, which
7. 7
   温度on cooling

実験手順

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

出典