Hydrochloric Acid → Ammonia

Participants

Reaction Steps

Hydrochloric acid (10.0 ml of a 2M solution in diethyl ether) was added in one portion to a stirred solution of di-tert-butyl[10-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-yl]imidodicarbonate (Preparation 2, 450 mg, 0.59 mmol) at room temperature in dichloromethane (5 ml) under a nitrogen atmosphere. The reaction was stirred for 2 hours and the solvent removed in vacuo, the residue was dissolved in ethyl acetate (30 ml) and saturated aqueous sodium hydrogen carbonate (20 ml). The organics were separated, washed with water (10 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 (90/10/1.0 by volume) to furnish the title compound as a glass, 180 mg.

Provenance & Evidence