[reaction: see text] The iridium catalyst [Ir(Cp*)Cl2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in a one-pot process.

A wide range of aldoximes has been converted into the corresponding amides using the ruthenium-based catalyst Ru(PPh3)3(CO)H2/dppe/TsOH. The amides are generated in high yield and selectivity, with catalyst loading as low as 0.04 mol %.

(S)-3-(5-Oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinolin-4-yl)benzonitrile is a potassium-channel opener developed for the treatment of urinary urge incontinence. The key step in the synthesis is an unsymmetrical Hantzsch reaction to give a 2-hydroxy-1,2,3,4-tetrahydropyridine. In our study the order of addition of reagents was found to be critical in the optimisation of the yield and the control of impurity levels in this reaction. The yield and the relative charges of the reagents were further optimised by the use of factorial experimental design. The chemistry has been scaled up to plant scale to produce multikilogram amounts of the Hantzsch product in close to 60% yield.