Water → Tert-butyl 4-(3,3-dibromoallyl)piperidine-1-carboxylate

Temperature

0 °C

Carbon tetrabromide (46.7 g, 141 mmol) was dissolved in 200 mL dichloromethane. The solution was cooled in an ice-water bath and triphenylphosphine (73.9 g, 282 mmol) in 200 mL dichloromethane was introduced via an addition funnel over 20 min. The reaction mixture was stirred at 0° C. for 10 min and a solution of tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate (16 g, 70.4 mmol) in 100 mL dichloromethane was added via an addition funnel. The solution was stirred at 0° C. for 1 hour. Water (250 mL) was added and aqueous layer was extracted 3 times with 100 mL dichloromethane. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. 300 mL ether was added to the residue, and the resulting suspension was filtered. The solid was washed 3 times with 150 mL ether. The combined filtrate was concentrated and passed through a plug of silica gel, washed thoroughly with 10% acetone/hexanes to afford yellow oil which was used without further purification.

1. temperatureThe solution was cooled in an ice-water bath
2. stirringThe solution was stirred at 0° C. for 1 hour
3. extractionaqueous layer was extracted 3 times with 100 mL dichloromethane
4. washThe combined organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. addition300 mL ether was added to the residue
9. filtrationthe resulting suspension was filtered
10. washThe solid was washed 3 times with 150 mL ether
11. concentrationThe combined filtrate was concentrated
12. washwashed thoroughly with 10% acetone/hexanes
13. customto afford yellow oil which
14. customwas used without further purification

ORD record

ord-b55196ccf55c42858dfdf2f6ad97aaf9

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343990B2