Methyl iodide → 4-tert-Butyl 2-methyl morpholine-2,4-dicarboxylate

HRID 456391Notes

Reaction equation

HRID 456391 reaction equation
CI.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:19](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:10]1([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:15][CH2:14][O:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid

Product 1

HCID 588174744-tert-Butyl 2-methyl morpholine-2,4-dicarboxylateYield 143.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (9.38 ml, 150 mmol) was added to a suspension of 4-(tert-butoxycarbonyl)-2-morpholinecarboxylic acid (14.5 g, 62.6 mmol) and dry potassium carbonate (17.3 g, 125 mmol) in dry dimethylformamide (DMF) (360 ml). The mixture was stirred over night, filtered through Celite and concentrated. The residue was partitioned between dichloromethane and water. The organic phase was dried over magnesium sulfate and concentrated to give 22 g of crude product.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-051f0f6500414de0a26c22475a10310e
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

Loading…