Iodine → Tropane

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.

1. customwas passed 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-ede8e4db2d514255a871a5207ec99caa

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013242