Reaktion #521023

Reaktionsgleichung

4-bromobutyrylferrocene

potassium iodide

triethylamine

→

desired compound

Ausbeute 15.0%

Ferrocene

Ausbeute 15.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed overnight
2. 2
   SonstigeUpon completion of reaction (as shown by TLC)
3. 3
   workup.ADDITIONSilica gel (1 g) was added
4. 4
   Sonstigethe solvent was evaporated
5. 5
   Wascheneluted with 5% methanol in methylene chloride

Vorschrift

To a solution of N-(9-azabicyclo[3.3.1] nonan-3a-yl)-N′-(2-methoxy-5-methylphenyl) carbamate (350 mg, 1.15 mmol) in toluene (10 mL) was added 4-bromobutyrylferrocene (385 mg, 1.15 mmol), potassium iodide (166 mg, 1.00 mmol), and triethylamine (500 mg, 4.94 mmol). The reaction mixture was refluxed overnight. Upon completion of reaction (as shown by TLC), the mixture was cooled to room temperature. Silica gel (1 g) was added, and the solvent was evaporated. The resulting solid was layered onto a silica gel column and eluted with 5% methanol in methylene chloride. The desired compound was isolated in 15 % yield (100 mg): mp 94-95° C.; 1H NMR (300 MHz, CDCl3) δ 7.89 (s, 1H), 7.13 (s, 1H), 6.75-6.84 (m, 2H), 5.19-5.21 (m, 1H), 4.80 (s, 2H), 4.56 (s, 2H), 4.21 (s, 5H), 3.92 (s, 3H), 3.65 (s, 2H), 3.16-3.24 (m, 2H), 2.90-2.98 (m, 4H), 2.40-2.52 (m, 3H), 2.31 (s, 3H), 2.00-2.06 (m, 3H), 1.70-1.78 (m, 4H).

Quelle