Methyl iodide → HCID 21981791, compound

HRID 1636517Notes

Reaction equation

HRID 1636517 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 1 N aq sodium bicarbonate. The combined aqueous phases were chilled and acidified to pH 3 with 1 N 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) δ 3.28 (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 1 N 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-93ebcebd281e4f5d91e9c1d90c723896
Source dataset
uspto-grants-2000_03
Patent number
US06034216

Reaction notes

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