Reaktion #5459

Reaktionsgleichung

water

sodium hydroxide

water

1-azabicyclo[3.3.1]nonane-5-carboxylic acid ethyl ester

lithium aluminum hydride tetrahydrofuran

→

colorless solid

Ausbeute 98.0%

1-Azabicyclo[3.3.1]nonane-5-methanol

Ausbeute 98.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige5° C
2. 2
   Temperaturrefluxed for 45 minutes
3. 3
   Temperaturcooled (0° C.)
4. 4
   FiltrationThe suspension was filtered through Celite
5. 5
   Waschenthe solid was washed with tetrahydrofuran
6. 6
   EinengenThe filtrate was concentrated in vacuo

Vorschrift

A solution of 1-azabicyclo[3.3.1]nonane-5-carboxylic acid ethyl ester (9.08 g, 46 mmol) in anhydrous tetrahydrofuran (25 mL) was added dropwise to a cooled (-10° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (50 mL, 50 mmol) in a 3-neck, 250-mL flask under nitrogen at a rate to keep the reaction temperature below, 5° C. The mixture was stirred for 15 minutes at room temperature, refluxed for 45 minutes, cooled (0° C.), and carefully treated dropwise with water (2 mL), 15% sodium hydroxide (2 mL), and water (6 mL). The suspension was filtered through Celite and the solid was washed with tetrahydrofuran. The filtrate was concentrated in vacuo to afford 6.99 g (98%) of colorless solid; mp 64.0°-65.5° C.

Quelle