Ethyl (3S)-piperidine-3-carboxylate → HCID 50923564, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-(4-(oxiran-2-yl)-2-(trifluoromethyl)phenyl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole (50 mg, 0.107 mmol) in EtOH (5 mL) was added (S)-ethyl piperidine-3-carboxylate (50.5 mg, 0.321 mmol). The reaction mixture was heated at 80° C. overnight and solvents were removed in vacuo. The mixture was treated with 6N HCl in MeCN at 50° C. for 24 h. The reaction mixture was filtered and purified by HPLC. HPLC conditions: PHENOMENEX® Luna C18 5 micron column (250×30 mm); 25-100% CH3CN/water (0.1% TFA); 25 minute gradient; 30 mL/min. Isolated fractions with correct mass were freeze-dried overnight to yield 24 mg of (3S)-1-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)-3-(trifluoromethyl)phenyl)ethyl)piperidine-3-carboxylic acid as a TFA salt. 1H NMR (400 MHz, MeOH-d3) δ ppm 7.99-8.06 (1H, m), 7.91-7.96 (1H, m), 7.81-7.90 (1H, m), 7.59 (2H, d, J=6.59 Hz), 7.44-7.56 (3H, m), 3.69-4.04 (1H, m), 3.34-3.64 (3H, m), 3.26-3.35 (2H, m), 2.72-3.14 (2H, m), 2.00-2.22 (1H, m), 1.75-2.00 (2H, m), 1.56 (1H, t, J=12.81 Hz). MS (m+1)=597. HPLC Peak RT=3.4 minutes (Analytical Method A). Purity=92%.

Provenance & Evidence