Sodium Hydroxide → HCID 24780865, compound

Participants

Reaction Steps

A solution of the methyl {(2S,4R)-1-[(1R)-4-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)pentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Step 1, 142 mg, 0.29 mmol) and aqueous NaOH (4N, 220 μl, 0.88 mmol) in MeOH (2 ml) was heated at 60° C. for 3 hrs. After cooling to RT the MeOH was removed in vacuo, and the residue was partitioned between CH2Cl2/H2O. 2N HCl (˜0.5 ml) was added. The pH of the aqueous layer was adjusted to ˜pH7 with saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (×4). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 4-8% MeOH/CH2Cl2) to give the acid (113 mg) as a colourless solid. 1H NMR (360 MHz, CD3OD): δ 0.65-0.75 (1H, m), 0.83-1.15 (11H, m), 1.18-1.55 (6H, m), 1.73-1.93 (5H, m), 2.18-2.30 (3H, m), 2.44 (1H, brt, J 12), 3.11 (1H, brd, J 12), 3.35 (1H, d, J 11), 3.43 (1H, d, J 12), 3.79 (2H, d, J 6.7), 3.88 (1H, d, J 8.0), 7.53 (2H, d, J 7.6), 7.63 (2H, d, J 8.2); M/Z (ES+) 470 (MH+).

Provenance & Evidence