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

HRID 278946Notes

Reaction equation

HRID 278946 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)[O-: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 10566517HCID 10566517, compound

Product 1

HCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxideYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 420 ml of chloroform, 42.0 g (0.14 mole) of the 1′-tert-butoxycarbonyl-spiro[benzo[c]thiophene-1(3H),4′-piperidine] obtained in Referential Example 1(a) were dissolved, followed by the addition of 12.7 g (0.15 mole) of sodium bicarbonate. To the resulting mixture, 28.0 g (85% content, 0.14 mole) of m-chloroperbenzoic acid were added in small portions under ice-cooling. After stirring of the mixture for 30 minutes under ice-cooling, 10 g of potassium iodide were added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain a residue. The residue was purified by chromatography on a silica gel column (eluting solvent; n-hexane: ethyl acetate=1:1), whereby 42 g of the title compound were obtained as white crystals.

Workup

  1. dissolutionwere dissolved
  2. temperaturecooling
  3. temperaturecooling
  4. stirringthe mixture was stirred at room temperature for 30 minutes
  5. washThe reaction mixture was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customto obtain a residue
  9. customThe residue was purified by chromatography on a silica gel column (eluting solvent; n-hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7e429d3c2f4c45fb8ce1a00384e2d848
Source dataset
uspto-grants-2002_03
Patent number
US06362179B1

Reaction notes

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