Diisopropylamine → HCID 58285090, compound

6.52 g of diisopropylamine was dissolved in 24 mL of tetrahydrofuran, and the solution was cooled on ice. Then, 2.91 mL of n-butyl lithium (a 2.66 M hexane solution) was added thereto. After stirring at the same temperature for 30 minutes, the mixture was kept at −78° C. To the reaction mixture, 3.87 mL of trimethylsilyldiazomethane (a 2 M hexane solution) was added at the same temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, a solution prepared by dissolving 1 g of 1-tert-butylpyrimidin-4-one (synthesized by the method as described in J. Org. Chem., 2005, 70, 1930) in 6 mL of tetrahydrofuran was added at the same temperature, and the mixture was stirred at the same temperature for 1.5 hours, and heated overnight under reflux. To the reaction mixture, water was added, and the mixture was extracted with 200 mL of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate. Then, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 120 mL of ethyl acetate, and 24 g of silica gel was added thereto at room temperature. The mixture was stirred at the same temperature for 1.5 hours. The insolubles were filtered, and the filtrate was concentrated under reduced pressure to obtain 830 mg of 1-tert-butylpiperidin-4-carboaldehyde [87-1] (hereinafter, referred to as the compound [87-1]).

1. temperaturethe solution was cooled on ice
2. customwas kept at −78° C
3. stirringthe mixture was stirred at the same temperature for 1 hour
4. customTo the reaction mixture, a solution prepared
5. customsynthesized by the method
6. stirringthe mixture was stirred at the same temperature for 1.5 hours
7. temperatureheated overnight
8. temperatureunder reflux
9. extractionthe mixture was extracted with 200 mL of ethyl acetate
10. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
11. filtrationThen, the insolubles were filtered
12. concentrationthe filtrate was concentrated under reduced pressure
13. dissolutionThe obtained residue was dissolved in 120 mL of ethyl acetate
14. addition24 g of silica gel was added
15. customat room temperature
16. stirringThe mixture was stirred at the same temperature for 1.5 hours
17. filtrationThe insolubles were filtered
18. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-cd886a820ee64a17ab90e6ecda9fb708

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2