Lithium Hydroxide → HCID 178525705, compound

Participants

Reaction Conditions

Reaction Steps

The cis/trans mixture of 4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid ethyl esters (D) (600 mg, 2.1 mmol) was dissolved in a minimal amount of THF (5 mL) and mixed with concentrated aqueous LiOH (2 mL). The reaction was stirred vigorously and heated at 65° C. for 3 h. After cooling and concentration, the crude material was dissolved in 1:1 water/CH3CN and subjected to preparative reverse-phase HPLC to yield (E) cis-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid (200 mg, 37%): 1H NMR (400 MHz, CD3OD) δ 7.77 (m, 2 H), 7.60 (m, 2H), 3.11 (d, 2H), 2.62 (m, 1H), 2.10 (m, 3H), 1.65 (m, 4H), 1.43 (m, 2H); mass spectrum m/z 259 [(M+H)+; calcd for C15H19N2O2: 259].

Provenance & Evidence