Acetic Acid → HCID 58474352, compound

Participants

Reaction Steps

To a solution of 6-bromonicotinaldehyde (1.25 g, 6.72 mmol) in DCM (25 mL) was added 3-aminopropan-1-ol (1.514 g, 20.16 mmol) and acetic acid (0.385 mL, 6.72 mmol), and the reaction mixture was stirred for 10 min. Sodium triacetoxyborohydride (3.56 g, 16.80 mmol) was added and the reaction mixture was stirred at RT overnight. The reaction mixture was then diluted with EtOAc and extracted with water. The organic phase was discarded. The aqueous phase was concentrated and the resultant solid was stirred with a mixture of DCM and acetone then filtered. The filtrate was collected, dried over Na2SO4, and concentrated to give a yellowish material, which upon trituration with Et2O afforded title compound 196 (0.9 g, 55% yield) as an off-white solid. MS: 246 (MH+).

Provenance & Evidence