Sodium Thiosulfate → 4-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenol

HRID 412548Notes

Reaction equation

HRID 412548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:21]=[CH:20][C:17](C=O)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:30])C=1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:21]=[CH:20][C:17]([OH:30])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 185365054-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)benzaldehyde

Product 1

HCID 185363684-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenolYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzaldehyde (500 mg) in methylene chloride (10 ml) was added 70% 3-chloroperbenzoic acid (712 mg) with ice-cooling, and the mixture was stirred at room temperature for 4.5 hours. After completion of the reaction, aqueous sodium hydrogencarbonate solution and aqueous sodium thiosulfate solution were added, and the mixture was extracted with methylene chloride and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was dissolved in methanol (3.4 ml) and thereto was added 1N aqueous sodium hydroxide solution (1.7 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10% aqueous citric acid solution was added, and the mixture was extracted with chloroform and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained solid was washed with diethyl ether and dried under reduced pressure to give the title compound (350 mg).

Workup

  1. temperaturecooling
  2. additionwere added
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed successively with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. dissolutionThe obtained residue was dissolved in methanol (3.4 ml)
  8. additionwas added 1N aqueous sodium hydroxide solution (1.7 ml)
  9. stirringthe mixture was stirred at room temperature for 1 hour
  10. customAfter completion of the reaction, 10% aqueous citric acid solution
  11. additionwas added
  12. extractionthe mixture was extracted with chloroform
  13. washwashed successively with water and saturated brine
  14. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  15. customthe solvent was evaporated
  16. washThe obtained solid was washed with diethyl ether
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-47e83552dc44454a8eebfe95d7564c83
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…