Potassium Iodide → 1'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

HRID 1275151Notes

Reaction equation

HRID 1275151 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[OH:23].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[I-].[K+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 105665171'-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4'-piperidine]

Product 1

HCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

42.0 g (0.14 mole) of 1'-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4'-piperidine] [prepared as described in step (a) above] were dissolved in 420 ml of chloroform, and 12.7 g (0.15 mole) of sodium hydrogencarbonate were added thereto. 28.0 g (0.14 mole) of m-chloroperbenzoic acid (purity 85%) were then added little by little, whilst ice-cooling. The mixture was then stirred for 30 minutes, whilst ice-cooling, after which 10 g of potassium iodide were added, and the mixture was stirred for a further 30 minutes at room temperature. The reaction mixture was washed with water and then with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 42 g of the title compound as white crystals, melting at 103-107° C. (after crystallisation from diisopropyl ether).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for a further 30 minutes at room temperature
  4. washThe reaction mixture was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  6. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography
  8. additionby volume mixture of hexane and ethyl acetate as the eluent
  9. customto give
  10. custom42 g of the title compound as white crystals, melting at 103-107° C. (after crystallisation from diisopropyl ether)

Sources & evidence

ORD record
ord-22fbe713f9ab49cd8161bed5e8449c28
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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