Toluene → HCID 58909951, compound

HRID 1295975Notes

Reaction equation

HRID 1295975 reaction equation
CI.[C:3]([C:7]1[CH:8]=[C:9]([C:25](=[O:27])[CH3:26])[CH:10]=[C:11]([N:15]2[CH2:19][C@@H:18]([O:20][CH2:21][O:22][CH3:23])[C@H:17]([OH:24])[CH2:16]2)[C:12]=1[O:13][CH3:14])([CH3:6])([CH3:5])[CH3:4].[C:28]1(C)C=CC=CC=1.C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:3]([C:7]1[CH:8]=[C:9]([C:25](=[O:27])[CH3:26])[CH:10]=[C:11]([N:15]2[CH2:19][C@@H:18]([O:20][CH2:21][O:22][CH3:23])[C@H:17]([O:24][CH3:28])[CH2:16]2)[C:12]=1[O:13][CH3:14])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 58910015HCID 58910015, compound

Product 1

HCID 58909951HCID 58909951, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Tetra-n-butylammonium bromide (227 mg, 0.704 mmol) and methyl iodide (0.18 ml, 2.9 mmol) were added to a mixed solvent of 1-{3-(tert-butyl)-5-[(3R,4R)-3-hydroxy-4-(methoxymethoxy)tetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (496 mg, 1.41 mmol) in a toluene (3 ml) −50% aqueous NaOH (3 ml) mixed solvent in that order at room temperature and the mixture was stirred for 64 hours. It was then diluted with water, extraction was performed with ethyl acetate and the extract was washed with brine. After drying with 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 (397 mg, 77%) as a light yellow oil.

Workup

  1. additionmixed solvent in that order at room temperature
  2. washthe extract was washed with brine
  3. dry with materialAfter drying with anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-006b54249b54412ba52542701fdff420
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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