Sodium Hydroxide → HCID 86628111, compound

Participants

Reaction Steps

Diethyl (1S,2S,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexane-1,2-dicarboxylate (3.0 g, 5.19 mmol, intermediate from Example 1, Step 1) was dissolved 50 mL methanol. NaOH (20 mL, 5 N) was added at room temperature. The mixture was stirred for 20 hr. Solvent methanol and water were removed under vacuum. The residue was dissolved in 100 mL 2N aq. HCl. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give the title compound (2.7 g). 1H-NMR (CDCl3) δ: 7.71 (1H, s), 7.21 (2H, s), 6.98 (2H, m), 6.85 (2H, m), 4.43 (1H, q, J=6.4 Hz), 3.75 (2H, q, J=7.1 Hz), 3.35 (1H, m), 2.92-2.72 (3H, m), 2.38 (1H, m), 2.30 (1H, m), 1.60 (2H, m), 1.33 (3H, d, J=6.4 Hz), 0.80 (3H, t, J=7.1 Hz).

Provenance & Evidence