Reaction #499765

Reaction equation

citric acid

lithium diisopropylamide tetrahydrofuran

4-cyanopiperidine-1-carboxylic acid tert-butyl ester

allyl bromide

→

title compound

4-Allyl-4-cyanopiperidine-1-carboxylic Acid tert-Butyl Ester

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 30 min and at room temperature for 1 hour
2. 2
   workup.ADDITIONwas added
3. 3
   Extractionthe mixture was extracted with diethyl ether
4. 4
   WashThe organic layer was washed with saturated brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   OtherThe solvent was evaporated
7. 7
   Otherthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
8. 8
   Otherdried under reduced pressure

Procedure

To a solution of 2M lithium diisopropylamide-tetrahydrofuran solution (9.96 ml) in tetrahydrofuran (20 ml) was dropwise added a solution of 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (3.5 g) in tetrahydrofuran (15 ml) at −78° C. and under argon atmosphere, and the mixture was stirred at room temperature for 30 min. Then, allyl bromide (2.15 ml) was added at −78° C., and the mixture was stirred at the same temperature for 30 min and at room temperature for 1 hour. After completion of the reaction, 10% aqueous citric acid was added and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) and dried under reduced pressure to give the title compound (3.5 g).

Source