Water → HCID 18427519, compound

HRID 1275148Notes

Reaction equation

HRID 1275148 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=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:23]OS([O-])=O.[K+].O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2(=[O:23])=[O:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18427519HCID 18427519, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

190 mg (0.59 mmole) of 1'-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4'-piperidine]-2-oxide [prepared as described in Preparation 4(a)] were dissolved in 30 ml of methanol, and 10 ml of an aqueous solution containing 270 mg (1.77 mmole) of Oxone (trade mark) were added. The reaction mixture was stirred at room temperature for 5 days, after which it was poured into water and then extracted twice with chloroform. The organic extract was separated and then dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by thin-layer chromatography, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent, to give 175 mg (yield 88%) of the title compound as white crystals.

Workup

  1. additionwere added
  2. extractionextracted twice with chloroform
  3. extractionThe organic extract
  4. customwas separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by thin-layer chromatography
  8. additionby volume mixture of ethyl acetate and hexane as the developing solvent

Sources & evidence

ORD record
ord-4722acfc639e42d0bb8ae4943f1038b7
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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