Neopentyl alcohol → 3-(6-Hepten-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Participants

Reaction Steps

Diethyl azodicarboxylate (0.5 g) was added dropwise over 1 minute to a stirred solution of triphenylphosphine (0.75 g) in tetrahydrofuran (20 ml) at -78° C. under a nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and then 6-hepten-1-ol (0.36 g) was added dropwise over 1 minute, followed by stirring at -78° C. for a further 5 minutes. Neopentanol (0.12 g) was added to the reaction mixture, followed by 3-azabicyclo[3.1.0]hexane-2,4dione (0.32 g) and stirring was continued for a further 5 minutes at -78° C. The reaction mixture was warmed to room temperature and stirred overnight. The volatiles were removed by evaporation in vacuo and the residue was triturated with hexane/dichloromethane and then filtered. The filtrate was evaporated in vacuo and then purified by chromatography on silica gel using 20% ethyl acetate/hexane as eluant. The title compound was obtained as a colourless oil (boiling point 150-160° C. @ 1 mmHg).

Provenance & Evidence