Triethylamine → Ethyl(1S,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-formylcyclohexanecarboxylate

Participants

Reaction Steps

To a solution of oxalyl chloride (0.22 mL, 2.6 mmol) in 40 mL dichloromethane was slowly added under nitrogen DMSO (0.13 mL, 1.8 mmol) at −78° C. The mixture was stirred for 5 min at the same temperature. Intermediate alcohol obtained from Step B (0.46 g, 8.6 mmol) in 15 mL dichloromethane was added by injection. Stirring continued at −78° C. for 20 min. Triethylamine (0.48 mL, 3.4 mmol) was added. The cooling bath was removed and the mixture was stirred until the temperature rose to −0° C. The reaction was quenched with sat. aq. NH4Cl. The organic layer was separated and the aqueous was extracted with dichloromethane (40 mL×2). The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give 0.45 g title compound which was used without further purification. 1H-NMR (CDCl3): δ: 9.64 (1H, s), 7.71 (1H, s), 7.22 (2H, s), 7.00 (2H, m), 6.86 (2H, m), 4.43 (1H, q, J=6.4 Hz), 3.80 (2H, q, J=7.1 Hz), 3.34 (1H, m), 2.84 (2H, m), 2.66 (1H, m), 2.46 (1H, m), 2.32 (1H, m), 1.64 (2H, m), 1.42 (1H, m), 1.35 (3H, d, J=6.4 Hz), 0.82 (3H, t, J=7.1 Hz).

Provenance & Evidence