Water → Ammonia

Participants

Reaction Steps

To a solution of N-(3-{6-methyl-3-[(E)-3-(3-methyl-2-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 134, 100 mg, 0.240 mmol) in anhydrous tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.25 ml, 0.25 mmol) and the reaction mixture was stirred at room temperature for 7 h. The rapidly stirred reaction mixture was treated sequentially with water (0.25 ml), sodium carbonate (250 mg) and ethyl acetate (2.5 ml). The reaction mixture was left to stir overnight and then was filtered and concentrated in vacuo. This was purified by chromatography using silica gel (2 g) eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1) to afford the title compound as a very pale yellow oil (60 mg, 62%).

Provenance & Evidence