Iodine → Tropane

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.

1. customwas padded through for 10 min
2. extractionextracted with CH2Cl2 (5×20)
3. dry with materialThe combined organic extracts were dried (MgSO4)
4. customevaporated

ORD record

ord-48919ef77d8c41049c9feebcbffc51c8

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013242