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

Temperatur

60 °C

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).

1. additionwas added dropwise
2. temperaturewhile cooling on ice
3. extractionafter extraction with ethyl acetate (20 mL)
4. washthe extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure

ORD-Eintrag

ord-f040a2d2832f4304ab912427de10da89

Quelldatensatz

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07601843B2