Aniline → HCID 86649084, compound

Participants

Reaction Steps

In a flamed-dried round bottom flask equipped with a rubber septum in order to maintain a nitrogen atmosphere was added 2a (58.8 mg, 0.2 mmol) and aniline (43.7 μl, 0.48 mmol) dissolved in 5 ml of anhydrous MeOH. The reaction was stirred for 10 minutes, then NaCNBH3 (40.2 mg, 0.64 mmol) was added. The reaction was allowed to stir for 5 hours while maintaining pH 7 through addition of acetic acid when required. NaHCO3 was then carefully added to the reaction mixture and stirred for 5 minutes. Water was added and the aqueous mixture was extracted 3 times with Et2O. The collected organic phases were washed with water, then brine, and dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using flash column chromatography (silica gel; 5% MeOH in CH2Cl2) to afford the title compound as a white solid in 99% yield. Mp=96-97° C. 1H NMR (200 MHz. CDCl3) δ:7.40-7.10 (m, 7H), 6.78-6.62 (m, 3H), 3.51 (dd, J=13.6 Hz, 4.2 Hz, 1H), 3.4 (very bs, 2H), 3.28 (dd, J=13.6 Hz, 7.5 Hz, 1H), 2.86 (d, J=2.8 Hz, 1H), 2.50-2.35 (m, 1H) ppm. 13C NMR (50 MHz. CDCl3) δ: 148.3, 139.7, 129.5, 129.4, 128.8, 127.4, 125.8, 118.1, 115.3, 113.2, 46.4, 40.3, 38.0 ppm. Rf=0.14 (7:3 hexanes/EtOAc).

Provenance & Evidence