p-Toluenesulfonic acid → 1-[1-(1H-1,2,4-triazol-1-ylmethyl) tricyclo[3.3.1.03,7]non-3-yl]ethanone

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Reaction Steps

A stirred solution of 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole (2.6 g, 9.09 mmol) obtained from Step I and p-toluenesulfonic acid (0.16 g) in acetone (36 mL) was refluxed for 4 h. The volatiles were removed under reduced pressure and the residue was diluted with ethylacetate, washed with 10% aq. NaHCO3 and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-[1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (2.2 g, 86% yield) as a viscous liquid. m/z (M+1) 246; 1H NMR (CDCl3) 300 MHz δ 7.99 (s, 1H), 7.93 (s, 1H), 4.10 (s, 2H), 2.75-2.65 (m, 1H), 2.49-2.42 (m, 1H), 2.16 (s, 3H), 2.0-1.45 (m, 10H). 13C NMR (CDCl3) 75 MHz δ 211.0, 151.6, 143.6, 61.6, 56.9, 48.2, 45.9, 45.7, 42.6, 41.9, 37.3, 36.6, 26.3.

Provenance & Evidence