Sodium borohydride → (5-Bromo-2-(2-ethylpiperidin-1-YL)phenyl)methanol

Participants

Reaction Steps

To a solution of 5-bromo-2-(2-ethylpiperidin-1-yl)benzaldehyde (obtained in step 1, 10 g, 0.0484 mol) in methanol (100 mL) under nitrogen, was added sodium borohydride (1.28 g, 0.0484 mol) at 0° C. in portions. After being stirred at room temperature for a period of 1 h, the reaction mixture was evaporated to remove methanol. The resulting crude product was taken in water (100 mL) and extracted in ethyl acetate. The separated organic layer was washed with water, dried over sodium sulphate and concentrated under reduced pressure to afford the titled compound as yellow liquid (8.8 g, 88%). 1H NMR (DMSO-d6, 400 MHz) δ 7.54-7.55 (1H, s), 7.34-7.54 (1H, m), 7.07-7.09 (1H, d), 5.17-5.20 (1H, t), 4.59-4.64 (1H, d), 4.43-4.48 (1H, d), 2.77-2.84 (2H, m), 2.442-2.449 (1H, m), 1.74 (2H, t), 1.53-1.56 (2H, t), 1.32-1.34 (2H, m), 1.15-1.19 (2H, m), 0.60-0.64 (3H, t).

Provenance & Evidence