Potassium Hydroxide → HCID 25271115, compound

Participants

Reaction Conditions

Reaction Steps

To compound 48a, 2-(5-{1-[4-(4-Fluoro-phenoxy)-benzyl]-piperidin-3-yl}-4′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid ethyl ester (52.3 mg, 0.08 mmol) in EtOH (5.0 ml) was added 2M KOH (0.40 ml, 0.8 mmol). The reaction was heated to 78° C. for 3 hour, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, salt exchange with 1N HCl (aqueous) gave the product as a white lyophilate, (41 mg, 76%). 1H NMR (400 MHz, MeOD) δ ppm 0.90-0.96 (m, 6 H) 1.51 (ddd, J=13.08, 6.72, 6.60 Hz, 1 H) 1.68 (dt, J=13.76, 6.94 Hz, 1 H) 1.88-1.93 (m, 2 H) 1.95-2.03 (m, 1 H) 2.11 (s, 2 H) 3.06 (d, J=2.93 Hz, 2 H) 3.22 (t, J=12.96 Hz, 1 H) 3.48-3.57 (m, 2 H) 3.77 (t, J=7.70 Hz, 1 H) 4.33 (s, 2 H) 7.00-7.10 (m, 5 H) 7.14 (d, J=1.96 Hz, 1 H) 7.24-7.34 (m, 2 H) 7.44-7.50 (m, 2 H) 7.58 (s, 1 H) 7.74-7.83 (m, 4 H), Calcd for C37H37F4NO3 (M+H) 619.69, Found 620.4.

Provenance & Evidence