Chloromethyl Methyl Ether → HCID 58910015, compound

HRID 1295974Notes

Reaction equation

HRID 1295974 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([C:14]1[CH:15]=[C:16]([C:29](=[O:31])[CH3:30])[CH:17]=[C:18]([N:22]2[CH2:26][C@@H:25]([OH:27])[C@H:24]([OH:28])[CH2:23]2)[C:19]=1[O:20][CH3:21])([CH3:13])([CH3:12])[CH3:11].[CH2:32](Cl)[O:33][CH3:34].C(OCC)(=O)C>C(Cl)Cl.O>[C:10]([C:14]1[CH:15]=[C:16]([C:29](=[O:31])[CH3:30])[CH:17]=[C:18]([N:22]2[CH2:26][C@@H:25]([O:27][CH2:32][O:33][CH3:34])[C@H:24]([OH:28])[CH2:23]2)[C:19]=1[O:20][CH3:21])([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 58910051HCID 58910051, compound

Product 1

HCID 58910015HCID 58910015, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (2.3 ml, 13 mmol) was added to a solution of the 1-{3-(tert-butyl)-5-[(3R,4R)-3,4-dihydroxytetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (1.32 g, 4.29 mmol) in methylene chloride (10 ml) while cooling on ice, and then MOMCl (0.49 ml, 6.5 mmol) was added dropwise and the mixture was stirred at the same temperature for 10 minutes and then at room temperature for 2.5 hours. After completion of the reaction, it was diluted with water and extraction was performed with ethyl acetate. After washing with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (496 mg, 33%) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. waitat room temperature for 2.5 hours
  3. customAfter completion of the reaction, it
  4. washAfter washing with brine
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2b4ff4466d11471d89420d45ea0f59f2
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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