Imidazole → 6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

6-{4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde (1.5 g, 5.47 mmol) was dissolved in DMF (5.47 ml), and imidazole (0.558 g, 8.20 mmol) was added. The mixture was cooled to 0° C., TBDMS-Cl (0.989 g, 6.56 mmol) added and the mixture was allowed to warm to RT and stirred overnight. The mixture was diluted with 4:1 water:saturated sodium bicarbonate (100 ml), extracted with EtOAc (3×75 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vac. The residue was purified by column chromatography on silica gel, Biotage 50 g, using a gradient eluant of 0-100% EtOAc/hexanes to afford the title compound. LC/MS (m/z): 389 (M+H)+.

Provenance & Evidence