Methyl iodide → 1-tert-Butyl 3-methyl piperidine-1,3-dicarboxylate

HRID 1689906Notes

Reaction equation

HRID 1689906 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[CH3:17][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)=[O:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 235906521-tert-Butyl 3-methyl piperidine-1,3-dicarboxylateYield 93.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Amine preparation: To a solution of 1-BOC-3-piperidine carboxylic acid (3.0 g) in DMF (25 mL) was added potassium carbonate (3.62 g) followed by iodomethane (4.07 mL). After 2.5 h the reaction was diluted with water and extracted into diethyl ether. The organic layer was washed with brine, separated and dried (MgSO4). The solvent was evaporated to give piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2.98 g).

Workup

  1. extractionextracted into diethyl ether
  2. washThe organic layer was washed with brine
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-428e2117b76f4caa80ed312c3e624abe
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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