Piperidine → 3-Methoxy-4-piperidin-1-ylmethylphenol

Participants

Reaction Steps

To a pre-stirred solution of 4-hydroxy-2-methoxybenzaldehyde (1.02 g, 6.7 mmol), titanium isopropoxide (2.14 mL, 7.0 mmol) and piperidine (0.70 mL, 7.0 mmol) in DCM (20 mL) was added sodium triacetoxyborohydride (2.84 g, 13.4 mmol) in portions. After 3 h the reaction mixture was quenched by the addition of methanol (1.0 mL) and then the solvents were removed under reduced pressure to afford a residue. The resultant residue was then loaded onto an SCX-2 cartridge (10 g) and eluted with 2N ammonia in methanol to afford the title compound (456 mg, 30%). 1H NMR (CD3OD, 300 MHz): 7.17 (d, J=8.3 Hz, 1H), 6.51 (d, J=2.3 Hz, 1H), 6.43 (dd, J=8.2, 2.2 Hz, 1H), 4.07 (s, 2H), 3.84 (s, 3H), 3.16-2.99 (m, 4H), 1.84-1.73 (m, 4H), 1.67-1.56 (m, 2H).

Provenance & Evidence