Triethylamine → 4-{[(2,3-dihydro-1H-inden-2-ylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

Participants

Reaction Steps

2-Aminoindane hydrochloride (166 mg, 1.1×0.891 mmol) was suspended in solution of VII (304.2 mg, 0.891 mmol) in anhydrous THF (10 mL), triethylamine (198 mg, 275 μL, 2.2×0.891 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The mixture was 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 afford 134 mg (42%) white solid, 14: mp=114-116° C. (uncorrected); Rf=0.45 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 7.20 (bs, 2H), 7.15 (m, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.93 (d, 1H), 6.90 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.51 (bs, 2H), 3.81 (s, 3H, OCH3), 3.28 (dd, 3J=16 Hz, 4J=7.1 Hz, 2H), 2.80 (dd, 3J=16 Hz, 4J=4.5 Hz, 2H, NCH2), and 2.29 (s, 3H). Exact mass (ESI) calculated for C20H22NO5 [M+H]=356.1492. found 356.1496.

Provenance & Evidence