Sodium Hydroxide → 1-Benzyl-1,7-diazaspiro(4.4)nonane

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydride (1.98 g, 52.2 mmol) was added in portions, under argon, to a ice bath cooled solution of 6-benzyl-2,6-diazaspiro[4.4]nonan-1-one (4.00 g, 17.4 mmol) in dry THF (100 mL). The addition funnel was replaced with a reflux condenser, and the mixture was heated at reflux for 24 h. The mixture was cooled to 0° C. and treated drop-wise (caution: exothermic reaction) with 10 M aqueous sodium hydroxide until hydrogen evolution ceased and the aluminate salts were granular. The mixture was stirred 1 h at 0° C. and filtered through Celite. The filtrate was dried (K2CO3) and concentrated, leaving 3.60 g (95.7%) of viscous, colorless liquid.

Provenance & Evidence