HCID 57791770, compound → HCID 54594082, compound

Temperature

60 °C

4-cyclobutoxypyridine (13) (3.8 g, 25.47 mmol) and rhodium 5% on alumina (0.38 g, 0.05 mmol) in EtOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 25° C. for 16 hours. GCMS analysis indicated no reaction so the mixture was heated to 60° C. for 5 hours but analysis still only indicated trace product formation. Platinum Oxide (0.2 g) catalyst was added and stirred overnight at 60° C., 5 bar, but still no more product formation. The reaction mixture was transferred to a high pressure autoclave and heated overnight at 80° C. and 50 bar no more product formation was observed, thus temperature increased to 100° C. and pressure to 80 bar and left overnight bar but analysis, once more, indicated no more product formation. Thus added 5% ruthenium on Carbon (0.2 g) and heated overnight at 120° C. and 100 bar. Analysis showed no remaining starting material. The reaction was cooled and filtered and solvent evaporated to afford a yellow oil. The crude product was purified by distillation at 0.55 mBar, collecting fractions that distilled at 55° C. to afford the product as a colourless oil, which was used in next step without any further purification.

1. customno reaction so the mixture
2. temperatureheated overnight at 80° C.
3. temperaturethus temperature increased to 100° C.
4. waitpressure to 80 bar and left overnight bar
5. temperatureThe reaction was cooled
6. filtrationfiltered
7. customsolvent evaporated
8. customto afford a yellow oil
9. distillationThe crude product was purified by distillation at 0.55 mBar
10. customcollecting fractions
11. distillationthat distilled at 55° C.

ORD record

ord-8ccbf2d179134817821207e8576cf264

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2