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The vinyltin tropane (73 mg, 0.13 mmol) was dissolved in CH2Cl2 (9 mL) and argon was padded through for 10 min. Iodine (200 mg, 0.78 mmol) was added and the mixture was stirred at room temperature overnight. Aqueous Na2S2O3 solution was then added followed by NH4OH. The mixture was saturated with solid NaCl and extracted with CH2Cl2 (5×20). The combined organic extracts were dried (MgSO4) and evaporated. Chromratography of the residue over silica using 5-15% Et3N/ether gave lodonated tropane (26 mg, 51%): [α]25D=-71.0° (c 51, CHCl3); FTIR (neat) 3328, 2970, 2937, 2914, 1693 cm-1 ; 1H NMR (CDCl3) δ 7.35 (d, 1 H, J=15.0 Hz), 7.18 (d, 2 H, J=8.0 Hz), 7.09 (d, 2 H, J=8.0 Hz), 6.76 (d, 1 H, J=15.0 Hz), 3.69 (br s, 1 H), 3.57 (br d, 1 H, J=6.2 Hz), 3.17 (ddd, 1 H, J=11.3, 5.1, 5.1 Hz), 2.89 (br d, 1 H, J=5.5 Hz), 2.80 (b s, 1 H), 2.41 (ddd, 1 H, J=11.3, 11.3, 2.7 Hz), 2.28-1.93 (m, 3 H), 1.79-1.48 (m, 4 H), 0.68 (t, 3 H, J=6.9 Hz); 13C NMR (75.45 MHz, CDCl3) δ 214.7, 144.5, 142.8, 135.9, 127.9, 126.0, 76.2, 56.2, 55.7, 53.5, 38.6, 36.3, 33.6, 29.1, 27.5, 7.0; Anal. Calcd for C18H22NOI: C, 54.69; H, 5.61; N, 3.54. Found: C, 54.68; H, 5.66; N, 3.48. ##STR24## (E)-2β-Propanoyl-3β-[4-1-propynyl)phenyl]-8-azabicyclo[3.2.1]octane.
