Ethylamine → HCID 178465144, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of trans-4-(2-ethoxy-2-oxoethyl)-cyclohexanecarboxylic acid (Intermediate 6; 800 mg; 3.74 mmol) in CH2Cl2 (5 mL) was added oxalyl chloride (4.7 mL; 9.35 mmol), followed by a drop of DMF. After 3 h, the reaction was concentrated in vacuo, redissolved in THF (4 mL) and added dropwise to a stirred solution of ethylamine (2.0 M; 1.87 mL; 3.74 mmol) in THF (4 mL) at 0° C. Triethylamine (521 mL; 3.74 mmol) was added and the reaction stirred at 0° C. for 1 h. The reaction was quenched with H2O (25 mL) and extracted with EtOAc (3×50 mL). The combined extracted were washed with H2O and brine (25 mL each), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-75% EtOAc/hexanes gradient) to afford ethyl{trans-4-[(ethylamino)carbonyl]cyclohexyl}acetate as a white solid. LCMS=242.2 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 5.40 (s, 1 H), 4.14 (q, J=7.1 Hz, 2 H), 3.33-3.28 (m, 2 H), 2.21 (d, J=7.1 Hz, 2 H), 2.02 (tt, J=12.2, 3.4 Hz, 1 H), 1.94-1.78 (m, 5 H), 1.51 (qd, J=12.9, 3.2 Hz, 2 H), 1.27 (t, J=7.1 Hz, 3 H), 1.15 (t, J=7.3 Hz, 3 H), 1.07 (qd, J=12.8, 3.2 hz, 2 H).

Provenance & Evidence