2-Benzyl-2-azaspiro[4.4]nonane-1,4-dione → 2-Benzyl-2-azaspiro[4.4]nonan-4-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyl-2-azaspiro[4.4]nonane-1,4-dione (10.00 g, 41.10 mmol) in THF (240 mL) was added LiAlH4 (3.12 g, 80.20 mmol) portionwise at 0° C. After addition, the reaction mixture was stirred at 85° C. for 1 hour, then cooled down to 0° C. and quenched carefully with water (3.12 mL) and 15% KOH aqueous solution (3.12 mL) followed by another water (9.36 mL). After that, anhydrous MgSO4 (20 g) was added to the above mixture and stirred at rt for 15 min, then filtered through a pad of Celite. The filtrate was extracted with DCM (100 mL×3) and then the separated organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 5/1) to give the title compound as yellow oil (8.89 g, 93.5%).

Provenance & Evidence