反应详情

温度

0 °C

Methyl[2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamate (650 mg, 1.89 mmol) was dissolved in 20 mL of THF at 0° C. under nitrogen. 1M HCl/ether (2.65 mL, 2.65 mmol) was added dropwise and the solution stirred at 0° C. for 15 min. LiAlH4 (360 mg, 9.45 mmol) was then slowly added and the solution stirred at RT overnight. The reaction mixture was quenched at 0° C. by addition of MeOH (5 mL) followed by water (10 mL). The solution was diluted with EtOAc and washed with saturated NaHCO3 aqueous solution, brine and dried over anhydrous MgSO4. The solvent was evaporated and the product was used directly in the next step without further purification. Yield: 544 mg (96%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.08 (m, 2H), 1.17 (m, 3H), 1.53 (s, 9H), 1.64 (s, 2H), 1.67 (s, 2H), 1.72 (m, 2H), 2.02 (m, 1H), 2.86 (s, 3H), 4.06 (d, J=7.42 Hz, 2H), 6.60 (dd, J=8.69, 2.25 Hz, 1H), 6.99 (d, J=2.15 Hz, 1H), 7.12 (d, J=8.59 Hz, 1H).

1. stirringthe solution stirred at RT overnight
2. customThe reaction mixture was quenched at 0° C. by addition of MeOH (5 mL)
3. additionThe solution was diluted with EtOAc
4. washwashed with saturated NaHCO3 aqueous solution, brine
5. dry with materialdried over anhydrous MgSO4
6. customThe solvent was evaporated
7. customthe product was used directly in the next step without further purification