Water → HCID 58293363, compound

To a solution of 1-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (50.0 g) in N,N-dimethylformamide (500 ml) were added potassium carbonate (60.3 g) and allyl bromide (28.3 ml), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water (600 ml), and the mixture was extracted with ethyl acetate (600 ml). The organic layer was sequentially washed with water (600 ml) and saturated aqueous sodium chloride solution (400 ml). The separated aqueous layer was extracted with ethyl acetate (300 ml) again. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the resulting residue in n-hexane/ethyl acetate (4/1, 400 ml) was added silica gel (70 g), and the mixture was stirred at room temperature. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the titled compound (62.5 g).

1. extractionthe mixture was extracted with ethyl acetate (600 ml)
2. washThe organic layer was sequentially washed with water (600 ml) and saturated aqueous sodium chloride solution (400 ml)
3. extractionThe separated aqueous layer was extracted with ethyl acetate (300 ml) again
4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionTo a solution of the resulting residue in n-hexane/ethyl acetate (4/1, 400 ml) was added silica gel (70 g)
7. stirringthe mixture was stirred at room temperature
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-06a75bfb2af945d8ad77b8528e96541b

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609647B2