Triethylamine → HCID 89662240, compound

Participants

Reaction Steps

To a solution of 2-(2-allyl-6,6-dimethyl-cyclohexen-1-yl)acetic acid (80 mg, 0.38 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (103 mg, 0.54 mmol) and 1-hydroxy-7-azabenzotriazole (73 mg, 0.54 mmol) in DMF (2 mL) was added the pyrrolidine (55 mg, 0.77 mmol) followed by Et3N (117 mg, 1.15 mmol). The solution was stirred under Ar for 18 h. Water was added (20 mL) and the solution was extracted with ether (3*20 mL). The combined organic layers were washed with water (3*30 mL) and brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (4-1 to 3/1) to give the title compound as colourless oil (82 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 5.75 (1H, ddt, J=16.7, 10.5, 6.1, 6.1 Hz), 4.93 (2H, m, J=19.1, 1.8 Hz), 4.93 (0H, dd, J=8.1, 1.8 Hz), 3.44 (4H, td, J=6.8, 4.0 Hz), 2.93 (2H, s), 2.64 (2H, d, J=5.9 Hz), 1.89-2.02 (4H, m), 1.82 (2H, quin, J=6.6 Hz), 1.58 (2H, d, J=11.7 Hz), 1.43-1.50 (2H, m) 0.90-0.99 (6H, s) ppm.

Provenance & Evidence