Sodium → Ibutilide

Participants

Reaction Steps

A stirred suspension of lithium aluminum hydride (0.86 g, 0.0227 mol) in dry tetrahydrofuran (30 ml) under nitrogen is cooled to 0° to -5° C. and treated dropwise during 25 minutes with a solution of N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide as prepared in Preparation 3 (3.0 g, 0.00757 mole) in THF (30 ml). After 2.5 hours this mixture is treated dropwise with a saturated solution of sodium, potassium tartrate (10 ml) and then with ethyl acetate. The mixture is filtered and the solid is extracted with ethyl acetate. The organic solutions are dried (MgSO4) and concentrated; the residual product is combined to give 2.10 g of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide. By NMR this material is the same as an authentic sample obtained from another reaction and purified by silica gel chromatography with 0.5% NH4OH-6% MeOH--CH2Cl2.

Provenance & Evidence