Pyridine → 5-(1-Acetoxy-3-naphthylsulfonyl)-2-thia-5-azabicyclo-[2.2.1]heptane

Participants

Reaction Steps

4-Acetoxy-2-naphthalenesulfonyl chloride (375 mg, 2.50 mmol) and 2-thia-5-azabicyclo[2.2.1]heptane (711 mg, 2.50 mmol) were combined in CHCl3 (20 ml) and pyridine (20 ml) and the mixture was stirred at room temperature for 15 hr. At this time the solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc and 1N aq HCl. The EtOAc was then washed with saturated aq NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography using 3% acetone in CHCl3 to provide of the pure product as a white foam (321 mg, 35% yield): 1H NMR (CDCl3) δ 1.60-1.79 (2H, m, CH2), 2.48 (3H, s, CH3CO), 2.98 (1H, dd, J=7.78, 2.44 Hz, 1/2 CH2), 3.18 (1H, d, J=10.21 Hz, 1/2 CH2), 3.51 (2H, br m, CH2), 3.67 (1H, d, J=9.48 Hz, CH), 4.70 (1H, s, CH), 7.61-7.70 (3H, m, ArH), 7.94-8.05 (m, 2H, ArH, 8.28 (s, 1H, ArH).

Provenance & Evidence