Methanesulfonyl chloride → tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (800 mg) in CH2Cl2 (8 ml) was added methanesulfonyl chloride (0.44 ml) and TEA (1.6 ml) under ice bath cooling, and the mixture was stirred at room temperature for 4 hours. The reaction was quenched with aq. NaHCO2 solution and extracted with EtOAc. The organic phase was washed with brine and 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-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (398 mg) as a colorless oil.

Provenance & Evidence