Tri-o-tolylphosphine → Ammonia

Participants

Reaction Conditions

Reaction Steps

(3R)-3-[2-(Benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (WO9411337, 1.21 g, 2.50 mmol) was dissolved in acetonitrile (8 ml) and 6-(but-3-en-1-yloxy)hexanenitrile (Preparation 23, 708 mg, 4.20 mmol), diisopropylethylamine (0.64 ml, 3.75 mmol), palladium acetate (54 mg, 0.25 mmol) and tri(o-tolyl)phosphine (145 mg, 0.25 mmol) were added. The stirred reaction was heated at 90° C., under a nitrogen atmosphere, for 12 hours, cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml), brine (50 ml), dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 by volume) to furnish the title compound as an oil, 960 mg.

Provenance & Evidence