Sodium Triacetoxyborohydride

• m-Anisaldehyde [A0478]
• Dimethylamine Hydrochloride
• Sodium Acetate [S0559]
• Acetic Acid [A2035]
• Sodium Triacetoxyborohydride (= NaBH(OAc)₃) [S0394]
• THF

A solution of m-anisaldehyde (1.00 g, 7.34 mmol), dimethylamine hydrochloride (1.20 g, 14.7 mmol), sodium acetate (964 mg, 11.8 mmol) and acetic acid (253 µL, 4.41 mmol) in THF (30 mL) was stirred at 0 °C for 5 minutes and then sodium triacetoxyborohydride (3.42 g, 16.2 mmol) was added to the solution and stirred at room temperature for 1 hour. The reaction was quenched with sat. aq. NaHCO₃ and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate:hexane = 0:100 - 10:90) to give 1-(3-methoxyphenyl)-N,N-dimethylmethanamine as a colorless liquid (940 mg, 77% yield).

The reaction mixture was monitored by UPLC.

1-(3-Methoxyphenyl)-N,N-dimethylmethanamine

¹H NMR (270 MHz,DMSO); δ 7.22 (t, J = 7.8 Hz, 1H), 6.86-6.79 (m, 3H), 3.73 (s, 3H), 3.34 (s, 2H), 2.13 (s, 6H).

• Reductive amination of aldehydes and ketones by using sodium triacetoxyborohydride
  • A. F. Abdel-Magid, C. A. Maryanoff, K. G. Carson, Tetrahedron Lett. 1990, 31, 5595.