Hydrazine hydrate (1:1) → (3S)-1-[4-amino-3-(methyloxy)phenyl]-3-piperidinol

Participants

Reaction Steps

A solution of (3S)-1-[3-(methyloxy)-4-nitrophenyl]-3-piperidinol (3.90 g, 15.5 mmol), FeCl3 (0.630 g, 3.9 mmol), activated carbon (4.0 g), and hydrazine hydrate (3.9 mL, 124 mmol) was heated in methanol (100 mL) for 3 hours. Once the starting material was judged consumed by thin layer chromatography (10% MeOH/CH2CL2) the mixture was filtered over celite and concentrated to afford (3S)-1-[4-amino-3-(methyloxy)phenyl]-3-piperidinol as a dark purple solid (2.56 g, 11.53 mmol, 74% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.62-1.72 (m, 2 H), 1.75 (d, J=3.30 Hz, 1H), 1.93 (td, J=8.07, 4.40 Hz, 1 H), 2.44 (s, 2 H), 2.88 (s, 1 H), 2.93 (d, J=9.53 Hz, 1H), 2.99 (dd, J=10.81, 6.05 Hz, 2 H), 3.12 (d, J=10.63 Hz, 1 H), 3.84 (s, 3 H), 3.95 (s, 1 H), 6.44 (d, J=8.07 Hz, 1 H), 6.53 (s, 1 H), 6.64 (d, J=8.07 Hz, 1 H).

Provenance & Evidence