Reaktion #5458

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for one hour
2. 2
   Temperaturcooled (0° C.)
3. 3
   Filtrationthe mixture was filtered through Celite (the solid
4. 4
   Waschenwas washed with tetrahydrofuran) and
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto afford 6.50 g (92%) of viscous, colorless oil, which
7. 7
   Temperaturon cooling

Vorschrift

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.

Quelle