Phthalimide → N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide

Participants

Reaction Steps

1-(tert-Butoxycarbonyl)perhydroazepin-3-yl methanol (1.13 g, 4.93 mmol) was dissolved in tetrahydrofuran (10 mL). To this solution, triphenylphosphine (1.60 g, 5.92 mmol) and phthalimide (871 mg, 5.92 mmol) were added and the mixture was stirred at room temperature for 5 min. A 40% toluene solution of diethyl azodicarboxylate (3.23 mL, 7.40 mmol) was then added and the mixture was stirred at room temperature for 4 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.27 g (72%) of the desired compound as a colorless powder.

Provenance & Evidence