Pyridine → HCID 178472471, compound

Participants

Reaction Steps

Methyl chlorooxoacetate (72 μL, 0.77 mmol) was added in one portion to a stirred solution of ethyl cis-4-(4-aminophenoxy)cyclohexanecarboxylate (204 mg, 0.77 mmol) and pyridine (76 μL, 0.93 mmol) in DCM (5 mL) and the reaction mixture was stirred at room temperature for 1 h. Concentration in vacuo left a residue which was taken up in EtOAc (50 mL) and an aqueous solution of hydrochloric acid (1M, 30 mL) was added. The layers were separated and the organic layer was washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to leave an oil. The oil was purified by column chromatography, using a gradient of 10-70% ethyl acetate:isohexane as eluent, to give the title compound (Intermediate 108) (188 mg, 70%) as an oil; 1H NMR (CDCl3) δ 1.23-1.28 (3H, t), 1.57-1.68 (2H, m), 1.71-1.78 (2H, m), 1.92-2.04 (4H, m), 2.36-2.43 (1H, m), 3.96 (3H, s), 4.14 (2H, q), 4.43-4.45 (1H, m), 6.89-6.93 (2H, d), 7.51-7.55 (2H, d), 8.76 (1H, s); MS m/e (M−H)− 348.

Provenance & Evidence