Toluene → HCID 10765247, compound

HRID 1953042Notes

Reaction equation

HRID 1953042 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[C:12]([O:16][C:17]([N:19]1[C@@H:23]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH:22]=[C:21](Br)[C:20]1=[O:34])=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OC(C)C)(C)C.Cl.O>[C:12]([O:16][C:17]([N:19]1[C@@H:23]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[CH:22]=[C:21]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:20]1=[O:34])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 10811304HCID 10811304, compound

Product 1

HCID 10765247HCID 10765247, compoundYield 53.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

The diethanolamine complex of 4-methoxyphenyl boronic acid (2.5 grams, 11 mmol) was stirred in a mixture of diisopropyl ether (50 mL) and 1.5M aqueous hydrochloric acid solution (30 mL) for 2 hours. After separation of the aqueous layer, toluene (50 mL) was added and the mixture was concentrated to remove most of the diisopropyl ether. (5R)-3-Bromo-5-(tert-butyl-dimethylsilanyloxymethyl)-2-oxo-2,5-dihydropyrrole-1 -carboxylic acid tert-butyl ester (3.0 grams, 7.38 mmol), toluene (150 mL), and a solution of sodium carbonate (850 mg, 8 mmole) in water (20 mL) were added. After purging the solution of oxygen, tetrakis(triphenylphosphene)palladium (0) (250 mg) was added and the mixture was heated at reflux for 2.5 hours. The mixture was cooled and diluted with toluene and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated to a brown oil. The title compound (1.7 grams, 53%), was isolated by flash chromatography on silica gel eluting with methylene chloride.

Workup

  1. customAfter separation of the aqueous layer, toluene (50 mL)
  2. additionwas added
  3. concentrationthe mixture was concentrated
  4. customto remove most of the diisopropyl ether
  5. customAfter purging the solution of oxygen, tetrakis(triphenylphosphene)palladium (0) (250 mg)
  6. additionwas added
  7. temperaturethe mixture was heated
  8. temperatureat reflux for 2.5 hours
  9. temperatureThe mixture was cooled
  10. additiondiluted with toluene and water
  11. customThe organic layer was separated
  12. washwashed with brine
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-06594009c41a4618b747f7efbe5a82e6
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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