Carbon Dioxide → HCID 117832979, compound

An aqueous solution (32 ml) of heptane-2,6-dione (4.96 g, 38.7 mmol) and acetonedicarboxylic acid (10.74 g, 73.5 mmol) was injected into a sealed tube, and 27 M KOH (6 ml), an ammonium chloride (6.20 g, 116 mmol) aqueous solution (60 ml), and sodium acetate (3.81 g, 46.4 mmol) were added in order under ice-cooled condition. The mixture was then brought to pH 9 with a 1 g/ml KOH aqueous solution. The reaction liquid was stirred inside the sealed tube in the dark at room temperature for 3 days. A 10% hydrochloric acid aqueous solution was slowly dropped until the carbon dioxide gas generation went to completion, and the mixture was washed with dichloromethane. After a separation procedure, the aqueous layer was brought to basic pH with a 10% sodium hydroxide aqueous solution, and extracted with dichloromethane. The organic layer was dried over potassium carbonate, concentrated under reduced pressure, and purified by silica gel column chromatography to give 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.84 g, 28%).

1. temperaturecooled condition
2. customThe reaction liquid
3. washthe mixture was washed with dichloromethane
4. customAfter a separation procedure
5. extractionextracted with dichloromethane
6. dry with materialThe organic layer was dried over potassium carbonate
7. concentrationconcentrated under reduced pressure
8. custompurified by silica gel column chromatography

ORD record

ord-30140be127be49d2ac0dbae603beedf8

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09114390B2