Water → {1-Azabicyclo[3.3.1]nonan-5-yl}methanol

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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.

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