Trifluoroacetic acid → 2-[1-(Phenylmethyl)-3-pyrrolidinyl]benzonitrile

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Reaction Steps

A solution of N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (16.62 g,70.0 mmol) in dichloromethane (15 mL) are added dropwise, over a 45-minute period, to a solution of 2-ethenylbenzonitrile (6.00 g, 46.0 retool) and trifluoroacetic acid (0.57 g, 5.0 retool) in dichloromethane (55 mL). The resulting solution was stirred at room temperature for an additional 10 to15 minutes, and then heated with saturated aqueous sodium bicarbonate solution (ca 10-15 mL). The organic layer was decanted, washed with water,and dried over anhydrous magnesium sulfate. Filtration and concentration ofthe solution provided an orange oil which was chromatographed (silica-gel, hexanes-ethyl acetate 5:1) to afford the title compound (6.95 g, 58%) as apale yellow oil. 1H-NMR (300 MHz, CDCl3): δ=1.80-1.92 (1H,m), 2.43-2.55 (1H, m), 2.63-2.75 (2H, m), 2.88-2.96 (2H, m), 3.71 (2H, AB quartet, JAB =13.0 Hz), 3.78-3.86 (1H, m), 7.25-7.41 (6H, m), 7.53-7.66 (3H, m).

Provenance & Evidence