4-Phenoxyphenol → HCID 69003419, compound

HRID 749980Notes

Reaction equation

HRID 749980 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[CH2:29][O:14][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 132544-PhenoxyphenolHCID 24758Sodium hydrideHCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 69003419HCID 69003419, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 4-phenoxyphenol (200 mg, 1.07 mmol) m DMF (3 mL) at 0-5° C. was added 60% NaH (75 mg, 1.875 mmol) at 0-5° C. The reaction mixture was stirred at rt for 15 min at 0-5° C. A solution of (R)-2-(Toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (382 mg, 1.074 mmol) in DMF (2 mL) was added to the above mixture at 0-5° C. The reaction mixture was warmed to it and then heated at 90° C. for 15 h. The mixture was concentrated, diluted with saturated aq NaHCO3 and extracted with ethyl acetate. The aqueous layer was re-extracted with ethylacetate. The combined organic layers were dried over anhy. MgSO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (256 mg, 64%); MS; m/z 370 (M+H) LCMS (UV)>90%.

Workup

  1. temperatureThe reaction mixture was warmed to it
  2. temperatureheated at 90° C. for 15 h
  3. concentrationThe mixture was concentrated
  4. additiondiluted with saturated aq NaHCO3
  5. extractionextracted with ethyl acetate
  6. extractionThe aqueous layer was re-extracted with ethylacetate
  7. customThe combined organic layers were dried over anhy
  8. customMgSO4 and the solvent was removed in vacuo
  9. customto obtain the crude mixture, which
  10. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9d21cafcf0e94410b9ae023b6d542a0c
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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