Benzophenone imine → HCID 86692535, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-(5-bromopyridin-2-yl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (7.1 g), palladium(II) acetate (554 mg), (±)-2-(di-tert-butylphosphino)-1,1′-binaphthyl (1.51 g), and tert-butoxysodium (2.79 g) in toluene (48 ml) was added benzophenone imine (3.42 ml), stirred at 120° C. for 7 hours, then ethanol (48 ml), hydroxylamine monohydrate (5.4 g), and sodium acetate (9.54 g) were added thereto at room temperature, and stirred for 3.5 hours. To the reaction solution was added water (48 ml), stirred, then an aqueous solution of sodium hydrogen carbonate was added thereto, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with basic silica gel chromatography (n-hexane/ethyl acetate) to give 4-(5-aminopyridin-2-yl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (4.0 g) as a white solid. 1H-NMR (DMSO-d6) δ (ppm): 1.40 (9H, s), 1.82-1.89 (2H, m), 2.08 (2H, J=12.8 Hz), 3.00 (2H, brs), 4.04 (2H, J=12.8 Hz), 6.96 (1H, dd, J=8.7, 3.1 Hz), 7.21 (1H, d, J=8.2 Hz), 7.92 (1H, d, J=2.6 Hz).

Provenance & Evidence