Trifluoroacetic acid → HCID 59837845, compound

Participants

Reaction Steps

To a solution of 3-(phenylmethyl)-3-azabicyclo[3.2.1]octane-6,7-dicarbaldehye bis (O-methyloxime) (Preparation 33, 5.0 g, 15.2 mmol) in dichloroethane (150 ml) was added trifluoroacetic acid (17 ml) and the reaction mixture was stirred under nitrogen at room temperature for 20 min. The reaction mixture was heated under reflux for 2 h and then concentrated to give a brown oil. Ethyl acetate (100 ml) was added and the solution was treated with saturated sodium carbonate solution (70 ml) the layers were separated and the organic layer washed with brine and dried (Na2SO4) and concentrated to give an oil (4.0 g). The crude oil was purified by flash chromatography using silica gel eluting with ethyl acetate to give the title compound as an orange oil (1.93 g, 51%).

Provenance & Evidence