Ammonium formate → HCID 22137324, compound

Participants

Reaction Steps

To a solution of N-(4-benzyloxy-phenyl)-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (7.39 g, 12.9 mol) in 300 mL methanol was added palladium black (0.800 g) and ammonium formate (8.15 g, 129 mmol). The reaction mixture was heated at reflux for 3 hr. and was cooled. The reaction mixture was filtered through diatomaceous earth with the aid of methanol (2×50 mL). The filtrate was concentrated and the residue was partitioned between 600 mL ethyl acetate and 250 mL water. The layers were separated and the organic layer was washed with water (2×300 mL) and saturated aqueous sodium chloride (1×300 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography (25% ethyl acetate/hexanes) afforded 5.00 g of the title compound of Step D. MS 482.2 (M+1)+

Provenance & Evidence