Ammonia → HCID 14723155, compound

Participants

Reaction Steps

1.00 g (2.47 mmol) of 3-(2-bromo-8α-ergolinyl)-1,1-diethylurea is dissolved in 10 ml of toluene, mixed with 90 mg (0.12 mmol) of 1,1'-bis(diphenylphosphino)-ferrocene palladium(II) chloride and stirred for 15 minutes at room temperature. Then 5.5 ml of triethylborane (1M solution in tetrahydrofuran) and 2.5 ml of 4N potassium hydroxide solution are added and the mixture is refluxed for 4 hours. The reaction mixture is acidified with 2N hydrochloric acid, made alkaline with concentrated ammonia and extracted with dichloromethane. The raw product, obtained after drying of the organic phases (sodium sulfate) and removal of the solvent in a vacuum, is chromatographed on silica gel. (dichloromethane/methanol 98:2). Yield after crystallization (ethyl acetate): 307 mg (35%) [α]D +47.6° (c=0.5 in chloroform).

Provenance & Evidence