HCID 67282369, compound → HCID 25018649, compound

Participants

Reaction Steps

A mixture of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.00 g, 3.19 mmol) and methanol (30 mL) was sonicated to give a clear solution. Pd/C (10 wt %, dry basis, on activated carbon, wet, Degussa type E101 NE/W, 0.158 g) was added. The debenzylation reaction was conducted under a hydrogen atmosphere pressurized to 50 psi. The reaction was completed in 20 min. The reaction mixture was diluted with methanol (30 mL), sonicated for 10 min. A CELITE™ bed was prepared on a sintered glass, and washed with 6M HCl (100 mL), followed by water (7×50 mL) and then methanol (2×50 mL) under suction. The reaction mixture was filtered through the pre-treated CELITE™ bed. The filtrate was collected and concentrated in vacuo to give 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid product (0.59 g, 83% yield, HPLC Method 1 (Example 24), RT=7.9 min, HPLC purity (peak percent area): 99.5% at λ=280 nm). 1H NMR (DMSO-d6) δ ppm: 11.72, (br s, 1H), 7.51 (s, 1H), 5.32 (q, J=7.4 Hz, 1H), 2.20 (s, 3H). MS-ESI (m/z) 224.2 [M+1]+, 206.2 (100%), 186.2, 178.2, 158.2.

Provenance & Evidence