反应详情

To a stirred, room temperature, solution of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinyl]-1-butanone (2.1 g, 3.9×10-3 mole) and methanol (80 ml) was added NaBH4 (0.42 g, 1.1×10-2 mole). After stirring overnight, the methanol was evaporated at reduced pressure. The concentrate was dissolved in a two phase mixture of EtOAc/H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc. The EtOAc extracts were combined, washed with saturated aqueous NaCl, and dried over anhydrous MgSO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a solid. Crystallization from cyclohexane/hexane afforded α-[1-[4-[4-(1,1-dimethylethyl)phenyl]-4-hydroxybutyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazole-2methanol as a colorless solid: 1.6 g (75%), m.p. 87°-90° C.

1. customthe methanol was evaporated at reduced pressure
2. dissolutionThe concentrate was dissolved in a two phase mixture of EtOAc/H2O
3. customThe layers were separated
4. extractionthe aqueous layer was re-extracted with EtOAc
5. washwashed with saturated aqueous NaCl
6. dry with materialdried over anhydrous MgSO4
7. customThe drying agent was removed by filtration
8. customthe filtrate was evaporated at reduced pressure
9. customleaving a solid
10. customCrystallization from cyclohexane/hexane