Methyl iodide → 1-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

HRID 408227Notes

Reaction equation

HRID 408227 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1.[CH3:32]I.[Cl-].[NH4+]>C1COCC1>[CH3:32][C:13]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:15][CH2:16][N:11]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:12]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylate

Product 1

HCID 534862661-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (12.9 mL, 12.9 mmol, 1M solution in THF) at −78° C. was added to 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (3.0 g, 10.3 mmol) in THF (20 mL), 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.

Workup

  1. waitAfter 2 hours at room temperature
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by chromatography on silica gel (hexane:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-6cac3eade4724b3b840ea65a8017da14
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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