Pyridine → Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylate

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Reaction Conditions

Reaction Steps

After dissolving methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate (0.1648 g, 0.735 mmol) and pyridine (0.0829 g, 1.05 mmol) in methylene chloride (5 mL), trifluoromethanesulfonic anhydride (0.185 mL, 1.11 mmol) was added dropwise while cooling on ice and the mixture was stirred for 1 hour. Water (10 mL) was added to the reaction mixture, and after extraction with ethyl acetate (20 mL), the extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order and dried over anhydrous magnesium sulfate, and then 4-(5-methylpyridin-2-yl)aminopiperidine (0.2995 g, 1.57 mmol) was mixed therewith and the solvent was distilled off under reduced pressure. The obtained yellow oil was heated at 60° C. for 1 hour. It was then subjected to chromatography (50 g Merck Art. 9385, methylene chloride:methanol:ammonia water=97:3:0.2) to obtain the title compound as a white solid (0.2398 g, 0.603 mmole) (82% yield).

Provenance & Evidence