Methyl iodide → HCID 70678264, compound

HRID 2271495Notes

Reaction equation

HRID 2271495 reaction equation
[CH3:1]I.[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([OH:23])[CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:7]=[CH:8][C:9]=1[Cl:10].[H-].[Na+]>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([O:23][CH3:1])[CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:15]2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 70678264HCID 70678264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (0.1 mL, 1.20 mmol) was slowly added to 15 mL of tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (200 mg, 0.602 mmol) and NaH (44 mg, 1.20 mmol) dissolved in a distilled methylene chloride solution at 0° C., and the mixture was stirred for 4 hours. Thereafter, purified water (3 ml) was added thereto, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with methylene chloride (3*30 mL), and the organic layer was washed with a saturated sodium chloride solution and distilled water once, respectively and dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain a colorless liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (4:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (4:1, v/v)).

Workup

  1. customThereafter, purified water (3 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. extractionThe reaction mixture was extracted with methylene chloride (3*30 mL)
  5. washthe organic layer was washed with a saturated sodium chloride solution
  6. distillationdistilled water once
  7. dry with materialrespectively and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by reduced pressure evaporation
  9. customto obtain a colorless liquid, which
  10. customwas purified by flash chromatography (n-hexane:ethyl acetate (4:1

Sources & evidence

ORD record
ord-ccfd9118a02646f197cd017dc6af7e63
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

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