Dimethylformamide → HCID 59396049, compound

Participants

Reaction Steps

To a solution of (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid-[(3,6R)-6-methylpiperidin-3-yl]methanol (1.2 g, 3.3 mmol), 2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.76 g, 4.0 mmol), 1H-benzotriazol-1-ol (0.71 g, 4.7 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (0.89 g, 4.7 mmol) in DMF (22 mL) was added N,N-diisopropyl-N-ethylamine (2.3 ml, 13 mmol). The mixture was stirred at ambient temperatures for 16 hours, then diluted with ethyl acetate and washed with brine (2×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with 0-3% methanol in dichloromethane to provide [(2R,5R)-5-(hydroxymethyl)-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone as a clear oil.

Provenance & Evidence