Reaction #1121804

Reaction equation

ammonium chloride

1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate

lithium bis(trimethylsilyl)amide

MeI

→

1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

Yield 75.0%

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 (hexane:ethyl acetate 4:1)

Procedure

To 1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate (3.45 g, 13.1 mmol) in THF (20 mL) was added lithium bis(trimethylsilyl)amide (16.4 mL, 16.4 mmol) in THF at −78° C., and the reaction was stirred at this temperature for 20 minutes. MeI (1.10 mL, 17.7 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 (hexane:ethyl acetate 4:1) to give 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 75% yield) as an oil.

Source