Trifluoroacetic acid → 1,1-Dimethylpropyl 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

To a solution of tert-butyl 4-[2-(4-methanesulfonyl-phenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 1) (30 mg, 0.067 mmol) in dry dichloromethane (0.35 mL) under N2 was added trifluoroacetic acid (0.35 mL). The mixture was stirred at room temperature for 2 hours and concentrated in vacuo. To a solution of the residue in dry tetrahydrofuran (0.7 mL) was added triethylamine (28 μL, 0.2 mmol) and di-tert-amyl dicarbonate (25 μL, 0.1 mmol). The mixture was stirred at room temperature for 3 hours, diluted with water (1 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound as a white crystal (28 mg, yield 91%).

1. concentrationconcentrated in vacuo
2. stirringThe mixture was stirred at room temperature for 3 hours
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

ORD-Eintrag

ord-7d0ab0edde834763a1aef8955ad7aca6

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08536176B2