1-Methylimidazole → tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-methyl-1H-imidazole (2 g) in THF (15 ml) was added 1.59 M n-butyllithium in n-hexane solution (18.4 ml) slowly under ice bath cooling, and the mixture was stirred at room temperature for 3 hours. To this reaction mixture was added tert-butyl 4-oxopiperidine-1-carboxylate (5.8 g) in THF (15 ml) solution and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with EtOAc and was washed with brine, and was dried over MgSO4. Solvent was removed in vacuo, and the residue was purified by silica gel column (CHCl3:MeOH=95:5 to 90:10) to give tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (4.02 g) as a pale yellow powder.

Provenance & Evidence