Allyl bromide → HCID 69437788, compound

Temperature

-78 °C

1-(1,1-Dimethylethyl) 3-ethyl 1,3-piperidinedicarboxylate (12.85 g, 50 mmol) in tetrahydrofuran (50 mL) was added slowly to a stirred, cooled (−78° C.) solution of potassium hexamethyldisilazide (14.96 g, 75 mmol) in tetrahydrofuran (75 mL). The mixture was stirred at −78° C. for 30 minutes, then 3-bromo-1-propene (6.49 mL, 9.07 g, 75 mmol) was added dropwise over 5 minutes. The mixture was stirred at −78° C. for 1 hour, then saturated aqueous ammonium chloride (200 mL) and water (100 mL) were added. The mixture was allowed to warm to room temperature and extracted with ethyl acetate (3×200 mL). The combined organic fractions were washed with aqueous citric acid (10%, 3×200 mL), saturated aqueous sodium hydrogen carbonate (200 mL) and brine (200 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give to give the title compound as a pale yellow oil (13.46 g, 91%). m/z (ES+) 298 (M+1).

1. stirringThe mixture was stirred at −78° C. for 1 hour
2. temperatureto warm to room temperature
3. extractionextracted with ethyl acetate (3×200 mL)
4. washThe combined organic fractions were washed with aqueous citric acid (10%, 3×200 mL), saturated aqueous sodium hydrogen carbonate (200 mL) and brine (200 mL)
5. dry with materialdried (MgSO4)
6. customthe solvent was evaporated under reduced pressure
7. customto give

ORD record

ord-949caec97dda4eeaa796adebdab952c5

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105507B2