Sodium Hydroxide → 5-Benzyl-5-azaspiro[2.4]heptan-7-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (7Z)-5-(phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione 7-(O-methyloxime) (assumed 3.1553 g, 12.92 mmol) in THF (130 mL) was added lithium aluminum hydride (1.58 g, 41.63 mmol). The mixture was heated at 65° C. and stirred for 3 h. The mixture was then cooled to 0° C., and Na2SO4.10H2O was added. The mixture was stirred overnight, and then 1 N aq. NaOH (6 mL) was added. The mixture was vigorously stirred for 30 min, and then extracted with DCM (3×50 mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide racemic crude 5-(phenylmethyl)-5-azaspiro[2.4]heptan-7-amine (2.5355 g, 97% for 2 steps) as a light yellow oil. LCMS: (M+H)+: 203.1.

Provenance & Evidence