1-azabicyclo[2.2.2]octan-2-ylmethanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminum hydride (0.1 mol, 3.9 g) was suspended in THF (200mL) in a 50 mL flask at 0° C. (VI) (0.03 mol, 5.76g) was added in small portions. After the addition, the reagents were refluxed under a nitrogen atmosphere for 12 hours, cooled to 0° C. followed by dropwise addition of water (3.8 mL) and NaOH (3.9 mL of a 15% aqueous solution). After stirring for 30 minutes, water (12 mL) was added to the reaction mixture followed by additional stirring for 30 minutes. The reaction mixture was filtered, and hot THF was used for additional washings of the precipitate. The filtrate obtained was dried over anhydrous potassium carbonate and filtered again. Removal of THF on a rotary evaporator yielded (VII) as a colorless oil (5.1 g). Distillation at 0.3 mm Hg yielded (VII) (2.75 g) as a clear oil. After the addition the reagents were refluxed under a nitrogen atmosphere for 12 hours by additional stirring for 30 minutes The reaction mixture was filtered The filtrate obtained was dried over anhydrous potassium carbonate filtered again Removal of THF on a rotary evaporator

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium aluminum hydride (0.1 mol, 3.9 g) was suspended in THF (200mL) in a 50 mL flask at 0° C. (VI) (0.03 mol, 5.76g) was added in small portions. After the addition, the reagents were refluxed under a nitrogen atmosphere for 12 hours, cooled to 0° C. followed by dropwise addition of water (3.8 mL) and NaOH (3.9 mL of a 15% aqueous solution). After stirring for 30 minutes, water (12 mL) was added to the reaction mixture followed by additional stirring for 30 minutes. The reaction mixture was filtered, and hot THF was used for additional washings of the precipitate. The filtrate obtained was dried over anhydrous potassium carbonate and filtered again. Removal of THF on a rotary evaporator yielded (VII) as a colorless oil (5.1 g). Distillation at 0.3 mm Hg yielded (VII) (2.75 g) as a clear oil. After the addition the reagents were refluxed under a nitrogen atmosphere for 12 hours by additional stirring for 30 minutes The reaction mixture was filtered The filtrate obtained was dried over anhydrous potassium carbonate filtered again Removal of THF on a rotary evaporator