Hydrogen Bromide → HCID 66732466, compound

Participants

Reaction Steps

Trans-benzyl 2-(2-methyl-2H-tetrazol-5-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (99 mg, 0.26 mmol) (from example 81, step 3) was dissolved in hydrogen bromide (33% in HOAc, 1.35 mL, 7.73 mmol) and reacted for 1 h. The mixture was evaporated and the residue was partitioned between water and EtOAc. The aqueous phase was purified by preparative HPLC on a Kromasil C8 column (10 μm 250×50 ID mm) using a gradient of 0-15% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-(Trans-2-(2-methyl-2H-tetrazol-5-yl)piperidin-4-yl)isoxazol-3(2H)-one (45 mg, 70%). 1H NMR (400 MHz, cd3od) δ 1.83-2.05 (m, 2H), 2.21-2.31 (m, 1H), 2.36-2.44 (m, 1H), 2.93-3.06 (m, 2H), 3.17-3.25 (m, 1H), 4.37 (s, 3H), 4.49 (t, 1H), 5.77 (s, 1H). HRMS Calcd for [C10H14N6O2+H]+: 251.1256. Found: 251.1262.

Provenance & Evidence