Reaction #1121801

Reaction equation

ammonium chloride

1-benzyl 3-ethyl piperidine-1,3-dicarboxylate

lithium bis(trimethylsilyl)amide

MeI

→

1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

Yield 98.6%

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.WAITAfter 2 hours at room temperature
2. 2
   Extractionextracted with ether
3. 3
   Washwashed with brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   OtherAfter removal of the solvent
6. 6
   Otherthe residue was purified by chromatography on silica gel (hexane:ethyl acetate 5:1)

Procedure

To 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (3.0 g, 10.3 mmol) in THF (20 mL) was added lithium bis(trimethylsilyl)amide (12.9 mL, 12.9 mmol) in THF at −78° C., and the reaction was stirred at this temperature for 20 minutes. MeI (0.867 mL, 13.9 mmol) was added, and the reaction was warmed to room temperature. After 2 hours at room temperature, the mixture was poured onto saturated ammonium chloride (20 mL) and extracted with ether, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography on silica gel (hexane:ethyl acetate 5:1) to give 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.1 g, 98% yield) as an oil.

Source