Isopropyl chloroformate → HCID 18182587, compound

Participants

Reaction Steps

To a cooled (0° C.) suspension of 3-(carboxy-methyl)-5-cyano-2,3-dihydrobenzofuran (300 mg, 1.5 mmol, reference example 9) in CH2Cl2 (4 mL) is added triethylamine (210 mL, 1.5 mmol) followed by isopropyl chloroformate (1.65 mL, 1 M in CH2Cl2). The resulting solution is stirred for 20 min then a further portion of triethylamine is added (455 mL, 3.3 mmol) followed by 4-aminomethyl biphenyl hydrochloride (330 mg, 1.5 mmol). The cold bath is removed and stirring continued for 5 h. The reaction mixture is then diluted with CH2Cl2, washed with water and brine, dried over MgSO4 and concentrated. The residue was triturated with ether and the solid filtered to give 400 mg of the title compound. 1H NMR (CDCl3) δ2.55 (dd, J=16, 8 Hz, 1H), 2.65 (dd, J=16, 6 Hz, 1H), 4.06 (m, 1H), 4.42 (dd, J=8, 7 Hz, 1H), 4.49 (dd, J=15, 6 Hz, 1H), 4.55 (dd, J=15, 6 Hz, 1H), 4.88 (t, J=8 Hz, 1H), 6.83 (m, 1H), 7.38 (m, 3H), 7.37 (m, 1H), 7.45 (m, 4H), 7.61 (m, 4H). MS (EI) m/z 368 (M+).

Provenance & Evidence