Ammonium Hydroxide → (3R)-1-[3-(aminomethyl)phenyl]pyrrolidin-3-ol

Participants

Reaction Steps

To 3-[(3R)-3-hydroxypyrrolidin-1-yl]benzonitrile (0.070 g, 0.37 mmol) and 5% rhodium on alumina (15 mg) in abs EtOH (5 mL) was added NH4OH (26%, 1 mL). The resulting mixture was stirred under H2 over night. A second portion of 5% rhodium on alumina (30 mg) was added and the stirring under H2 continued for 2 days. The mixture was filtered through Celite and concentrated to give 0.62 g (69%) of the title compound (purity ˜80%). 1H NMR (400 MHz, CD3OD) δ 7.10 (dd, 1H, J=8.1, 7.6 Hz), 6.56 (d, 1H, J=7.6 Hz), 6.51 (s, 1H), 6.42 (dd, 1H, J=8.1, 2.0 Hz), 4.47 (m, 1H), 3.69 (s, 1H), 3.47-3.36 (m, 2H), 3.32-3.24 (m, 1H), 3.17 (bd, 1H, J=9-7 Hz), 2.15-1.93 (m, 2H). 13C NMR (MeOH-d4) δ 149.7, 143.4, 130.3, 115.8, 111.8, 111.7, 71.7, 57.0, 46.9, 46.7, 34.9.

Provenance & Evidence