HCID 131730372, compound → 5-[(2S,4S)-2-(2-Methylpropyl)-4-piperidinyl]-3(2H)-isoxazolone

Participants

Reaction Steps

Racemic cis-methyl 2-isobutyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.29 g, 1.03 mmol) was stirred in HBr (12 mL, 33% in HOAc) for 24 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/min. The title compound (160 mg) was isolated. 1H NMR (600 MHz, d2o) δ 0.79 (2 d, 6H), 1.34-1.51 (m, 3H), 1.54-1.72 (m, 2H), 2.13 (m, 1H), 2.25 (m, 1H), 2.99 (m, 2H), 3.21 (m, 1H), 3.38 (m, 1H), 5.61 (s, 1H).

Provenance & Evidence