Methyl iodide → HCID 68308583, compound

HRID 2171702Notes

Reaction equation

HRID 2171702 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([O:9][CH:10]2[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[CH:5][CH:4]=1.[H-].[Na+].CI.[C:25](O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)(Cl)Cl.ClCCCl.O.CCOC(C)=O.C1COCC1>[NH:12]1[CH2:13][CH:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][O:1][CH3:25])=[N:8][CH:7]=2)[CH2:11]1

Participants

11

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 86686246tert-Butyl 3-((6-(hydroxymethyl)pyridin-3-yl)oxy)azetidine-1-carboxylate

Product 1

HCID 68308583HCID 68308583, compound

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3-{[6-(hydroxymethyl)pyridin-3-yl]oxy}azetidine-1-carboxylate (198 mg) was mixed with THF (3 ml), and sodium hydride (55% suspended in oil) (50 mg) was added thereto at 0° C., followed by stirring at 0° C. for 30 minutes. Methyl iodide (0.4 ml) was added to the reaction mixture, followed by stirring at room temperature for 3 hours. EtOAc and water were added to the reaction mixture, and the organic layer was dried over Na2SO4, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The purified product thus obtained was mixed with DCE (2.8 ml), and TFA (902 mg) was added thereto, followed by stirring at room temperature for 5 hours. CHCl3 and a 1 M aqueous NaOH solution were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain 5-(azetidin-3-yloxy)-2-(methoxymethyl)pyridine.

Workup

  1. additionwas added
  2. customat 0° C.
  3. stirringby stirring at room temperature for 3 hours
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  7. customThe purified product thus obtained
  8. additionwas added
  9. stirringby stirring at room temperature for 5 hours
  10. dry with materialthe organic layer was dried over Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customThe obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-4d83e9234f184cf7a34482b93c30a5f7
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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