Methyl iodide → Methyl 1-(diphenylmethyl)azetidine-3-carboxylate

HRID 2066271Notes

Reaction equation

HRID 2066271 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([C:18]([OH:20])=[O:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH:1]([N:14]1[CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:17]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acid

Product 1

HCID 2759842Methyl 1-(diphenylmethyl)azetidine-3-carboxylateYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzhydrylazetidine-3-carboxylic acid (4.20 g) in N,N-dimethylformamide (45 ml) were added potassium carbonate (6.53 g) and iodomethane (0.976 ml), followed by stirring at room temperature for 20.5 hr. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=5:1, then 3:1). Fractions containing the target compound were concentrated to provide the titled compound as yellow crystals (3.57 g, 80.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by silica gel column chromatography (eluent
  6. additionFractions containing the target compound
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-e3c0dd2bb0ba4931bcb8cfd6d0b37f95
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

Loading…