Ammonia → HCID 69735819, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 300 mL of freshly condensed liquid ammonia at −70° C. was added lithium metal (4.1 equiv.). The dark blue slurry was warmed to −45° C. and treated with a pre-cooled solution of 3-(benzyloxycarbonyl)-amino-2,3-dihydro-1-methyl-5-phenyl-1H-1-benzazepin-2-one (Example 4-AC, Steps A-C) in 30 mL distilled THF. After 10 min a solution of tert-butanol (4.0 equiv.) in distilled THF was added. After an additional 10 min the reaction was quenched with ammonium chloride. The cooling bath w as removed and the ammonia allowed to evaporate overnight. The contents were partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purified via liquid chromatography eluting with a gradient from 99:1 to 90:10 CH2Cl2/MeOH.

Provenance & Evidence