Methyl iodide → HCID 21981791, compound

HRID 482563Notes

Reaction equation

HRID 482563 reaction equation
[C:1]([CH:8]([CH2:12][CH2:13][NH2:14])[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:15]I.[H-].[Na+]>C1COCC1>[C:1]([CH:8]([CH2:12][CH2:13][NH:14][CH3:15])[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18470678HCID 18470678, compound

Product 1

HCID 21981791HCID 21981791, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 5.00 g (24.6 mmol) of BOC-4-aminobutyric acid in 75 mL of dry THF, was added 12.2 mL (197 mmol) of methyl iodide followed by 2.95 g (73.8 mmol, 60% dispersion in mineral oil) of sodium hydride, portionwise. The reaction was rapidly stirred at room temperature for 12 h and quenched by the careful addition of water. The mixture was partitioned between ether and water, and the organic phase extracted with 1N aq sodium bicarbonate. The combined aqueous phases were chilled and acidified to pH 3 with 1N sodium hydrogen sulfate, then extracted with two portions of ethyl acetate. The combined organics were washed successively with water, 5% aq sodium thiosulfate, water, brine, and then dried over anhydrous magnesium sulfate. Concentration in vacuo afforded 5.00 g (94%) of BOC-4-(N-methylamino)butyric acid. 1H NMR: (300 MHz, CDCl3) δ3.28 (2H, bt, J=7 Hz), 2.84 (3H, s), 2.36 (2H, t, J=7.5 Hz), 1.85 (2H, m), 1.45 (9H, s).

Workup

  1. customquenched by the careful addition of water
  2. customThe mixture was partitioned between ether and water
  3. extractionthe organic phase extracted with 1N aq sodium bicarbonate
  4. temperatureThe combined aqueous phases were chilled
  5. extractionextracted with two portions of ethyl acetate
  6. washThe combined organics were washed successively with water, 5% aq sodium thiosulfate, water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-db83a7591bbf4725b950fd07e0f41e92
Source dataset
uspto-grants-1998_08
Patent number
US05798337

Reaction notes

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