Methyl iodide → HCID 3387867, compound

HRID 1271235Notes

Reaction equation

HRID 1271235 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([OH:18])=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=O)([O-])O.[K+].CI>CN(C)C=O.O>[CH3:19][O:17][C:16]([CH:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 232388N-(Carbobenzyloxy)-DL-prolineHCID 516893Potassium Bicarbonate

Product 1

HCID 3387867HCID 3387867, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 28.83 g of (±)-N-benzyloxycarbonyl-2-pyrrolidine carboxylic acid in 180 ml of N,N-dimethylformamide, 23.23 g of potassium hydrogen carbonate and 10.8 ml of methyl iodide were added. After stirring at room temperature for 15 hours, the reaction solution was diluted with water and then extracted twice with diethyl ether. After the extract was washed with an aqueous 5% sodium hydrogen sulfite solution and water and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure to obtain 26.52 g of the desired compound as a yellowish oily substance.

Workup

  1. extractionextracted twice with diethyl ether
  2. washAfter the extract was washed with an aqueous 5% sodium hydrogen sulfite solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aa8d8c2c26e640baaf9d2c0f1d9f87a9
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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