Methyl iodide → 1-N-Boc-4-Piperidinecarboxylic acid methyl ester

HRID 555861Notes

Reaction equation

HRID 555861 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterYield 106%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (10.50 g, 45.8 mmol) in DMF (200 mL) was added potassium carbonate (6.33 g, 45.8 mmol) followed by iodomethane (3.42 mL, 55.0 mmol). The reaction was stirred under N2 at RT 3 h. The reaction was poured into 10% aqueous K2CO3 (500 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were washed with saturated NaCl (2×150 mL), dried (MgSO4) and concentrated to give 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (11.8 g, 48.5 mmol, 106% yield) as a light yellow oil.

Workup

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe combined organic layers were washed with saturated NaCl (2×150 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-caeff2f82c804981b784e921aa40e5e6
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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