Hydrochloric Acid → HCID 59201234, compound

Participants

Reaction Steps

A solution of LiOH (60 mg, 2.5 mmol) in H2O (1 ml) was added to a stirred solution of methyl {(2S,4R)-1-[(1S,2Z)-4-methyl-1-(3-methylbutyl)pent-2-en-1-yl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Example 2, Step 1, 210 mg, 0.46 mmol) in THF (2 ml) at RT. The mixture was stirred at RT for 18 hrs, then at 60° C. for 3 hrs. After cooling to RT 2N HCl was added and the THF was removed in vacuo. The residue was partitioned between CH2Cl2 and H2O. The pH of the aqueous layer was adjusted to ˜pH7 with saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (×3). The combined extracts were dried (Na2SO4) filtered and evaporated. The residue was purified by chromatography (silica, 4-10% MeOH/CH2Cl2) to give the acid (173 mg) as a colourless foam. 1H NMR (500 MHz, CD3OD): δ 0.69 (3H, d, J 6.6), 0.81-0.87 (9H, m), 1.04-1.18 (2H, m), 1.25 (1H, q, J 12.1), 1.34-1.46 (3H, m), 1.56-1.68 (2H, m), 1.82-1.89 (3H, m), 2.13-2.21 (2H, m), 2.60 (1H, t, J 11.5), 3.23 (1H, brd, J 10), 3.38 (1H, q, J 8.7), 3.63 (1H, d, J 9.6), 5.28 (1H, t, J 10.6), 5.37 (1H, t, J 10.6), 7.53 (2H, d, J 7.7), 7.65 (2H, t, J 8.2); M/Z (ES+) 440 (MH+).

Provenance & Evidence