3-Hydroxypiperidine → HCID 50923425, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of piperidin-3-ol (20.04 mg, 0.198 mmol) in DMSO (2 mL) was added tetrabutylammonium hydroxide (0.198 mL, 0.198 mmol). After 5 minutes, 2-bromo-1-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol, Int-I-C (30 mg, 0.066 mmol) was added. The reaction mixture was heated at 80° C. for 2 hours. 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; 20 mL/min to yield 22 mg of 1-(2-hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-ol as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (2H, d, J=8.13 Hz), 7.83 (2H, dd, J=8.02, 1.65 Hz), 7.58-7.73 (5H, m), 5.17-5.28 (1H, m), 4.10 (1H, d, J=14.72 Hz), 3.06-3.91 (5H, m), 2.95-3.06 (2H, m), 2.59-2.95 (2H, m), 1.77-2.21 (2H, m), 1.64-1.76 (2H, m), 1.16-1.42 (1H, m), 0.98 (3H, t, J=7.36 Hz). MS (m+1)=475. HPLC Peak RT=3.32 minutes (Analytical Method A). Purity=98%.

Provenance & Evidence