1-Methyl-1,4-cyclohexadiene → (R)-quinuclidin-3-yl((S)-phenyl(3-(piperidin-4-ylmethoxy)phenyl)methyl)carbamate

To a solution of benzyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)-amino)methyl)phenoxy)methyl)piperidine-1-carboxylate (1.32 g, 2.26 mmol) in ethanol (100 mL) was added palladium on charcoal (0.66 g) and stirred at room temperature for 10 minutes. 1-Methyl-1,4-cyclohexadiene (1.27 mL, 11.3 mmol) was added and the reaction mixture heated to reflux. The reaction mixture was stirred under reflux for 1 hour. The reaction mixture was allowed to cool and the suspension filtered. The filtrate was evaporated at reduced pressure to afford the title compound (1.05 g, 100%).

1. temperaturethe reaction mixture heated to reflux
2. stirringThe reaction mixture was stirred
3. temperatureunder reflux for 1 hour
4. temperatureto cool
5. filtrationthe suspension filtered
6. customThe filtrate was evaporated at reduced pressure

ORDレコード

ord-77bbac0e13e0450b9ecb6b41af83b3ec

出典データセット

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08980913B2