Triethylamine → [3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonate

Participants

Reaction Steps

To a solution of [3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methanol (2.0 g, 8.47 mmol) obtained in step IV, in THF (35 mL) at ice bath temperature, was sequentially added triethylamine (3.5 mL, 25.4 mmol), DMAP (52 mg, 0.42 mmol), and methanesulfonyl chloride (0.97 mL, 12.7 mmol). After stirring the reaction mixture at the same temperature for 0.5 h, it was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain title compound [3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonate (2.4 g) in 90% yield as viscous liquid. m/z (M+1) 317. IR cm−1 2954, 1461, 1356, 1216, 1174, 1048, 756. 1H NMR (CDCl3) 300 MHz δ 4.15-3.90 (m, 4H), 3.00 (s 3H), 2.44-2.36 (m 2H), 1.89-1.79 (m, 2H), 1.78-1.42 (m, 8H), 1.29 (s, 3H). 13C NMR (CDCl3) 75 MHz δ 112.1, 76.3, 64.95, 64.9, 57.3, 46.6, 45.3, 44.9, 44.5, 42.9, 39.8, 36.9, 36.7, 36.3, 20.

Provenance & Evidence