1-Methylimidazole → HCID 69411984, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methyl imidazole (350 uL, 4.4 mmol) in 15 mL of THF at −78° C. was added n-BuLi (1.5 mL of a 1.6 M solution in hexane, 2.4 mmol). After stirring for about 30 minutes, the solution was warmed to about 0° C. and then stirred for about 15 minutes. The mixture was then cooled to about −78° C. A solution of N-Boc-4-(2-formylphenyl)-piperazine (580 mg, 1.0 mmol) in 5 mL of THF was added via cannula The solution was allowed to warm slowly to r.t. overnight. After addition of saturated aqueous NH4Cl and brine, the solution was extracted with EtOAc (2×). The combined organic solutions were dried (Na2SO4), filtered and concentrated. Purification by silica gel chromatography (35 g SiO2, 0 to 10% 0.2 M NH3 in MeOH/CH2Cl2 over 30 min at 35 mL/min) afforded about 592 mg (1.59 mmol, 79%) of the alcohol as a colorless oil. LRMS (ESI+): 373.2 (M+1)

Provenance & Evidence