반응 #5458

반응 방정식

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

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도refluxed for one hour
2. 2
   온도cooled (0° C.)
3. 3
   여과the mixture was filtered through Celite (the solid
4. 4
   세척was washed with tetrahydrofuran) and
5. 5
   농축concentrated in vacuo
6. 6
   기타to afford 6.50 g (92%) of viscous, colorless oil, which
7. 7
   온도on cooling

실험 절차

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.

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