Methyl iodide → HCID 22914707, compound

HRID 1377713Notes

Reaction equation

HRID 1377713 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH3:28][O:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22914673HCID 22914673, compound

Product 1

HCID 22914707HCID 22914707, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-hydroxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoate from Step 2 above (1.50 g, 4.27 mmol) in DMF (40 mL) under N2 was added NaH (246 mg, 6.41 mmol). The reaction mixture was cooled, then CH3I (0.53 mL, 8.54 mmol) was added via syringe. The reaction mixture was warmed to ambient temperature and stirred for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified using pressurized silica gel column chromatography, eluting with 20% ethyl acetate in hexanes. Methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoate was obtained as a colorless oil which crystallized on standing overnight.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and aqueous NaHCO3
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified
  8. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-92c257b0d8944228bb65d7959264d3b3
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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