Borane;tetrahydrofuran → HCID 22141201, compound

Participants

Reaction Steps

To a solution of 3-hexyl-6-(3-nitrophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carbonitrile (Preparation 111, 250 mg, 0.732mmol) in anhydrous tetrahydrofuran (3 ml) stirred under nitrogen was added dropwise borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 2.9 ml, 2.9 mmol). The reaction mixture was heated at reflux for 2 h, before cooling and quenching with dry methanol (2 ml). The solution in methanol was heated under reflux for 18 h before concentrating in vacuo. The residue was again dissolved in methanol (ca 5 ml) and heated at reflux for 3 hours, followed by evaporation to dryness in vacuo. This process was repeated once more and extensive drying gave a brown oil (270 mg) which was purified by column chromatography on silica gel (13 g) eluting with dichloromethane:ethanol:0.88 ammonia (150:8:1). This gave the title compound as an orange oil (124 mg, 53%).

Provenance & Evidence