Methyl iodide → N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

HRID 1070515Notes

Reaction equation

HRID 1070515 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[CH2:12](N(CC)CC)C.CI>O1CCCC1>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH:10][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-amino-ethyl)-carbamic acid-tert-butyl ester (5 g) and triethylamine (6.5 ml) in tetrahydrofuran (1000 ml) at 0° C. was added methyliodide (1.94 ml) dropwise over a period of 1 hour. The mixture was allowed to warm to ambient temperature and stirred for 72 hours before removal of solvents by evaporation. The residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and solvent removed by evaporation to give the title compound (3.7 g).

Workup

  1. customThe residue was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4) and solvent
  4. customremoved by evaporation

Sources & evidence

ORD record
ord-499fb470ffe7411c96892cf2a8e76613
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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