Methyl iodide → HCID 22914645, compound

HRID 1377708Notes

Reaction equation

HRID 1377708 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:27]I>CN(C=O)C>[CH3:27][O:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[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 229147101,1-Dimethylethyl 3-[3-hydroxy-4-(methoxycarbonyl)phenoxy]-1-pyrrolidinecarboxylate

Product 1

HCID 22914645HCID 22914645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-hydroxy-4-(1-tert-butyloxycarbonyl-3-pyrrolidinyloxy)benzoate from Step 1 above (2.26 g, 6.70 mmol) in DMF (40 mL) under N2, was added NaH (400 mg, 10.1 mmol). The reaction mixture was cooled, and CH3I (0.83 mL, 13.4 mmol) was added via syringe. The reaction mixture was allowed to warm to ambient temperature, and stirred for an additional 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-pyrrolidinyloxy)-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-0108e254d40642efa7278bb6aecd68ee
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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