Pyrrolidine → 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-one

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Reaction Steps

A dry flask is charged with 7-bromo-3,4-dihydro-2H-naphthalen-1-one (CAS#32281-97-3, 0.102 g, 0.454 mmol), pyrrolidine (0.065 g, 0.909 mmol), 2-(di-t-butylphosphino)-biphenyl (0.020 g, 0.067 mmol), sodium tert-butoxide (0.087 g, 0.905 mmol) and toluene (3 mL). The flask is evacuated and filled with nitrogen three times. Pd2(dba)3 (0.041 g, 0.045 mmol) is added and the mixture is heated to reflux for 3 hours, whereupon the mixture is cooled to room temperature, diluted with dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-one; 1H NMR (400 MHz, CDCl3) δ ppm 1.99-2.03 (m, 4 H), 2.06-2.14 (m, 2 H), 2.60-2.65 (m, 2 H), 2.87 (t, J=6.1 Hz, 2 H), 3.28-3.35 (m, 4 H), 6.75 (dd, J=8.3, 2.8 Hz, 1 H), 7.12 (d, J=8.3 Hz, 1 H), 7.19 (d, J=2.8 Hz, 1 H).

Provenance & Evidence