HCID 68503570, compound → HCID 46938037, compound

Participants

Reaction Steps

To (2R,4S)-methyl 2-benzyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.47 g) was added HBr (33% in HOAc, 10 mL) and the solution was stirred for 16 h. The volatiles were concentrated and the residue purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 0-40% acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/minutes. The title compound was isolated (0.26 g, 29%): 1H NMR (600 MHz, dmso) δ 1.07 (m, 1H), 1.26-1.45 (m, 1H), 1.75 (m, 2H), 2.53 (m, 2H), 2.58-2.67 (m, 2H), 2.69 (m, 1H), 2.97 (m, 1H), 5.66 (s, 1H), 7.08-7.34 (m, 5H); [α]20D +67.8 (MeOH/H2O 1:1, c=1); HRMS Calculated for [C15H19N2O2]+: 259.1447. found: 259.1442.

Provenance & Evidence