HCID 9906491, compound → HCID 9861497, compound

Participants

Reaction Steps

To a solution of 762 mg (2.45 mmol) of ethyl 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanoate, the title compound of Example 1, in 12 mL of THF was added 2.45 mL of LAH (1M in THF) at ambient temperature, and the resulting mixture was stirred overnight. The reaction was quenched with water, extracted with ether, and the combined extracts were dried, and concentrated in vacuo. The residue was purified by silica gel chromatography to give 538 mg (83%) of 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-butanol as a colorless glass: 1H NMR (CDCl3) δ 1.52 (quintet, J=7.8 Hz, 2H), 1.92 (quintet, J=7.7 Hz, 2H), 3.61 (t, J=6.2 Hz, 2H), 4.29 (t, J=7.7 Hz, 2H), 6.06 (s, 2H), 6.93 (d, J=8.4 Hz, 1H), 7.15-7.25 (m, 2H), 7.25-7.37 (m, 2H), 7.38-7.45 (m, 1H), 7.78-7.88 (m, 1H); HRMS (FAB) Calc'd for M+H: 311.1396, found: 311.1447. Anal. Calc'd for [C18H18N2O3 +0.09 CH2Cl2 ]: C, 68.39; H, 5.77; N, 8.82. Found: C, 68.39; H, 5.81; N, 8.82.

Provenance & Evidence