Triethylamine → HCID 56847913, compound

Participants

Reaction Steps

To a stirred yellow solution of VII (293.8 mg, 0.861 mmol) in anhydrous THF (10 mL) was added cyclohexylmethanamine (165 mg, 123 μL, 1.1×0.861 mmol) and then, dropwise, triethylamine (96 mg, 133 μL, 1.1×0.861 mmol). The solution was stirred for 45 minutes at room temperature. The colorless solution was then diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to yield 150.2 mg (52%) of 13 as a clear colorless oil: Rf=0.55 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.98 (d, 3J=8.0 Hz, 1H), 6.95 (d, 1H), 6.91 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.75 (bs, 1H, NH), 3.81 (s, 3H, OCH3), 3.01 (t, 3J=6.4 Hz, 211, NCH2), 2.29 (s, 3H), 1.70-1.62 (m, 5H), 1.42 (bs, 1H), 1.23-1.11 (m, 3H) and 0.92 (q, 3J=11.5 Hz, 2H).

Provenance & Evidence