Ammonium formate → 6-Benzenesulfonyl-8-benzyl-1-phenyl-8-aza-bicyclo[3.2.1]octan-2-one

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Reaction Steps

To a 500 ml round bottom flask equipped with nitrogen inlet and condenser was placed 5.87 gm (13.68 mmol) of the 6-Benzenesulfonyl-8-benzyl-1-phenyl-8-aza-bicyclo[3.2.1]oct-3-en-2-one together with 150 ml of methanol, 17.25 gm (273.66 mmol) ammonium formate and 1.95 gm palladium hydroxide. The reaction mixture was heated under reflux for 1.5 hours and then cooled to room temperature. The suspension was filtered through a bed of celite which was then washed with methanol. The combined organics were evaporated in vacuo and the residue was taken up in chloroform and partitioned with saturated aqueous bicarbonate solution. The organics were washed with saturated brine solution and then dried over a bed of sodium sulfate. The mixture was filtered and the filtrate evaporated in vacuo. The residue was chromatographed on silica gel eluting with 8:2/hexane:ethyl acetate to afford 4.04 gm (68%) of an off white solid. 1H NMR (CDCl3, 400 MHz) δ 7.79 (d, 2H, J=7 Hz), 7.66 (t, 1H, J=7 Hz), 7.51 (t, 2H, J=8 Hz), 7.40–7.19 (m, 10H), 3.93 (br.s., 1H), 3.70 (d, 1H, J=15 Hz), 3.62 (t, 1H, J=7 Hz), 3.35 (d, 1H, J=14 Hz), 2.70–2.5 (m, 4H), 1.79–1.70 (m, 1H), 1.55 (br.s., 1H) ppm. Mass spectrum APCI m/z 432 (p+1).

Provenance & Evidence