Hydrochloric Acid → 3-Benzyl-3-azabicyclo[3.1.0]hexane

Participants

Reaction Conditions

Reaction Steps

A solution of iodine (2.27 g) in THF (27.9 mL) was added dropwise at 0° C. to a mixture of sodium borohydride (818 mg) in dry THF (45 mL) within 40 min. At this temperature, a solution of 3-benzyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione (750 mg) in THF (11.1 mL) was then added dropwise. Then the reaction mixture was heated for 6 h under reflux. The mixture was cooled to 0° C., and 3N HCl was carefully added. Then the reaction solution was neutralized with 2N sodium hydroxide solution. The aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 173.12 (C12H15N); MS (ESI): 174 (M+H+).

Provenance & Evidence