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

HRID 1712647Notes

Reaction equation

HRID 1712647 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[CH:9]([N:22]1[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH:9]([N:22]1[CH2:23][CH:24]([C:26]([O:28][CH3:1])=[O:27])[CH2:25]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=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

Potassium carbonate (6.53 g) and iodomethane (0.976 ml) were added to a solution of 1-benzhydrylazetidine-3-carboxylic acid (4.20 g) in N,N-dimethylformamide (45 ml), followed by stirring at room temperature for 20.5 hours. 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 distilled off, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=5:1, then 3:1). The fractions containing the target compound were concentrated to give the title compound (3.57 g, 80.8%) as yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-6c026da0dee645b797f0fbbdc1470e4e
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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