Toluene → HCID 67136588, compound

HRID 1295981Notes

Reaction equation

HRID 1295981 reaction equation
[CH2:1](I)[CH3:2].[C:4]([C:8]1[CH:9]=[C:10]([C:26](=[O:28])[CH3:27])[CH:11]=[C:12]([N:16]2[CH2:20][C@H:19]([O:21][CH2:22][O:23][CH3:24])[C@@H:18]([OH:25])[CH2:17]2)[C:13]=1[O:14][CH3:15])([CH3:7])([CH3:6])[CH3:5].C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:4]([C:8]1[CH:9]=[C:10]([C:26](=[O:28])[CH3:27])[CH:11]=[C:12]([N:16]2[CH2:20][C@H:19]([O:21][CH2:22][O:23][CH3:24])[C@@H:18]([O:25][CH2:1][CH3:2])[CH2:17]2)[C:13]=1[O:14][CH3:15])([CH3:7])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6340Iodoethane3×HCID 8857Ethyl AcetateHCID 67137822HCID 67137822, compound

Product 1

HCID 67136588HCID 67136588, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Tetra-n-butylammonium bromide (380 mg, 1.18 mmol) and ethyl iodide (0.4 ml, 5.0 mmol) were added to a solution of 1-{3-(tert-butyl)-5-[(3S,4S)-3-hydroxy-4-(methoxymethoxy)tetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (830 mg, 2.36 mmol) in a toluene (5 ml) −50% aqueous NaOH (5 ml) mixed solvent at room temperature in that order and the mixture was stirred for 19 hours. After further adding ethyl iodide (0.2 ml) and stirring for 9 hours, more ethyl iodide (0.2 ml) was added and stirring was continued for 60 hours. The mixture was 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 (650 mg, 73%) as a light yellow oil.

Workup

  1. additionmixed solvent at room temperature in that order
  2. stirringstirring for 9 hours
  3. stirringstirring
  4. waitwas continued for 60 hours
  5. washthe extract was washed with brine
  6. dry with materialAfter drying with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f7bb3cf36969457f98076c09529d9fcd
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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