Hydrochloric Acid → Ammonia

Participants

Reaction Steps

Di-tert-butyl{9-[4-({3-[hydroxy(diphenyl)methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}imidodicarbonate (Preparation 27, 1.7 g, 2.46 mmol) was dissolved ethanol (30 ml) and hydrogen chloride in ether (2M, 30 ml, 60 mmol) added. After stirring at room temperature for 18 hours the solvent was removed in vacuo, and the residue partitioned between dichloromethane (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml). The organic layer was separated, dried over magnesium sulphate, filtered 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 to 80:20:2, by volume) to furnish the title compound as a white solid, in 60% yield, 725 mg.

Provenance & Evidence