Naphthalene → Ammonia

Participants

Reaction Steps

Sodium (390 mg, 16.6 mmol) was added to a solution of naphthalene (2.61 g, 20.4 mmol) in 1,2-dimethoxyethane (25 ml), and the solution stirred at room temperature for 4 hours. This solution was then added dropwise to a cooled (−70° C.) solution of 4-methylphenyl 3-tetrahydro-2H-pyran-4-yl-1-azetidinesulfonate (EP 962457) (1 g, 3.39 mmol) in 1,2-dimethoxyethane (25 ml), and once the addition was complete, the mixture was stirred at −70° C. for 20 minutes. The reaction was allowed to warm to room temperature, the reaction quenched by the addition of water and concentrated under reduced pressure. The residual gum was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (80:20:3) as eluant to give the title compound as an off-white gum, 690 mg.

Provenance & Evidence