Potassium Carbonate → HCID 86746603, compound

HRID 1613167Notes

Reaction equation

HRID 1613167 reaction equation
[Cl-:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@H:4]([NH:10][C:11](=[O:26])[C:12](=[O:25])[C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=3)[N:15]([CH3:24])[CH:14]=1)[CH2:3]2.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Cl-:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@H:4]([NH:10][C:11](=[O:26])[C:12](=[O:25])[C:13]1[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=3)[N:15]([CH3:24])[CH:14]=1)[CH2:3]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 86746604HCID 86746604, compound

Product 1

HCID 86746603HCID 86746603, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

(S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-1-methyl-5-methoxy-α-oxo-3-indoleacetamide chloride (750 ml; 2.2 mmol) in 30 ml of methylene chloride was stirred and cooled to -70° C. A 1M solution of boron tribromide in methlene chloride (8.0 ml; 8.0 mmol) was added via a syringe. The solution was allowed to warm to ambient temperature and then stirred continuely for 4 days. The reaction mixture was then stirred for 1 hour with ice-cold water containing an excess of potassium carbonate. The layers were separated and the phenolic product was extracted from the methylene chloride layer into 5% aqueous sodium hydroxide. The aqueous layer was stirred and sodium bicarbonate was added until saturated. The product that precipitated was extracted into methylene chloride. The methylene chloride solution was dried over potassium carbonate, filtered and concentrated to leave 500 ml (1.5 mmol) of (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-1-methyl-5-hydroxy-α-oxo-3-indoleacetamide chloride, m.p. 282°-284° C., [α ]D25 -7.8° (H2O).

Workup

  1. temperatureto warm to ambient temperature
  2. customThe layers were separated
  3. extractionthe phenolic product was extracted from the methylene chloride layer into 5% aqueous sodium hydroxide
  4. stirringThe aqueous layer was stirred
  5. additionsodium bicarbonate was added until saturated
  6. customThe product that precipitated
  7. extractionwas extracted into methylene chloride
  8. dry with materialThe methylene chloride solution was dried over potassium carbonate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-185a2698fe7041aeab0822cffcd5beb2
Source dataset
uspto-grants-1993_03
Patent number
US05192770

Reaction notes

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