HCID 131730371, compound → HCID 46938040, compound

Participants

Reaction Steps

Racemic trans-methyl 2-isobutyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.39 g, 1.3 mmol) was stirred in HBr (33% in HOAc) 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 0-25% acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 10 minutes with a flow of 100 mL/minutes. The title compound (0.26 g) was isolated. 1H NMR (600 MHz, d2o) δ 0.76 (d, 3H), 0.79 (d, 3H), 1.14 (m, 1H), 1.33-1.41 (m, 1H), 1.45 (m, 1H), 1.59 (m, 1H), 1.76 (m, 1H), 1.98 (m, 1H), 2.06 (m, 1H), 2.21 (m, 1H), 3.04 (m, 2H), 3.14-3.31 (m, 4H), 5.67 (s, 1H).

Provenance & Evidence