Reaktion #478630

Reaktionsgleichung

tert-Butyl 4-(((5-bromo-4′-cyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

dimethylformamide

→

tert-Butyl 4-(((4′,5-dicyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed repeatedly
2. 2
   Temperaturthe reaction was heated at 90° C. for 1 h
3. 3
   Temperaturcooled to room temperature
4. 4
   Einengenconcentrated
5. 5
   SonstigeFlash chromatography on silica gel (30% ethyl acetate/hexanes) gave 15 mg (33%)

Vorschrift

tert-Butyl 4-(((5-bromo-4′-cyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (52 mg, 0.09 mmol), tetrakis(triphenylphosphine) palladium(0) (14 mg, 0.01 mmol), and zinc cyanide (12 mg, 0.1 mmol) were combined in dimethylformamide (1.5 mL). The reaction mixture was degassed repeatedly using the freeze-pump-thaw method. After warming to room temperature, the reaction was heated at 90° C. for 1 h, cooled to room temperature, and concentrated. Flash chromatography on silica gel (30% ethyl acetate/hexanes) gave 15 mg (33%). 1H-NMR (CDCl3, 300 MHz) δ 7.78-7.75 (m, 3H), 7.52-7.55 (m, 2H), 7.31-7.33 (m, 4H), 7.20-7.23 (m, 2H), 4.41 (s, 2H), 3.70-3.77 (m, 2H), 3.43 (s, 2H), 2.97-3.06 (m, 2H), 2.17-2.21 (m, 2H), 1.78-1.88 (m, 2H), 1.40 (s, 9H). Mass spec.: 508.28 (MH)+.

Quelle