Aluminium lithium hydride → 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-N-methyl-1H-benzimidazol-5-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate (0.781 g, 2.06 mmol) in THF was added LAH (0.32 g, 8.43 mmol) at 0° C. The mixture was stirred for 1 h at 0° C. and 2.5 h at reflux, cooled town to −78° C., and quenched with MeOH (5 mL) and H2O (5 mL). After adding Na2SO4 (10 g), the resulting mixture was stirred for 1 h at room temperature. After filtration and concentration, the residue was purified by MPLC using EtOAc on silica gel to give 641.7 mg (93%) of the title compound as an off-white solid. 1HNMR (CDCl3): δ 0.22 (m, 2H), 0.48 (m, 2H), 1.26 (m, 1H), 1.38 (t, J=7.0 Hz, 3H), 2.89 (s, 3H), 3.83 (d, J=6.6 Hz, 2H), 3.98 (q, J=7.0 Hz, 2H), 4.23 (s, 2H), 6.64 (dd, J=8.6, 2.2 Hz, 1H), 6.80 (d, J=8.6 Hz, 2H), 6.99 (d, J=2.1 Hz, 1H), 7.13 (m, 3H). MS (ESI) (M+H)+=336.42.

Provenance & Evidence