Reaction Steps
The vinyltin tropane (40 mg, 0.070 mmol) was dissolved in CH2Cl2 (5 mL) and argon was passed through for 10 min. Iodine (107 mg, 0.42 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. Chromatography of the residue over silica using 5-15% Et3N/ether gave iodonated tropane (16.2 mg, 57%): [α]25D=-97.3° (c 0.3, CHCl3); FTIR (neat) 2937, 2911, 1694, 1406 cm-1 ; 1H NMR (CDCl3) δ 7.34 (d, 2 H, J=8.1 Hz), 7.12 (d, 2H, J=8.1 Hz), 6.60 (s, 1 H), 3.73 (m, 1 H), 3.59 (br d, 1 H, J=5.1 Hz), 3.25 (ddd, 1 H, J=15, 5.5, 5.5 Hz), 2.90 (br d, 1 H, J=5.5 Hz), 2.69 (s, 3 H), 2.45 (ddd, 1 H, J=15, 15, 2.2 Hz), 2.22-1.95 (m, 3 H), 1.78-1.55 (m, 4 H), 0.68 (t, 3 H, J=7.3 Hz); 13C NMR (75.45 MHz, CDCl3) δ 215.2, 141.6, 136.8, 134.3, 128.6, 127.2, 100.0, 56.1, 55.7, 53.4, 38.9, 36.4, 35.3, 33.5, 29.0, 27.5, 7.0; Anal. Calcd for C19H24NOI: C, 55.75; H, 5.91; N, 3.42. Found: C, 55.97; H, 6.00; N, 3.25. ##STR27## (E)-2β-Propanoyl-3β-[4-(2-iodopropenyl)phenyl]-8-azabicyclo[3.2.1]octane.
