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Thiosulfuric acid, disodium salt, monohydrate → 1'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

HRID 747492
Notes
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Reaction equation

HRID 747492 reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH2:5][C:4]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][S:7]2)[CH2:3][CH2:2]1.[OH:22]OS([O-])=O.[K+].O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(Cl)Cl.CC(C)=O>[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:2][CH2:3][C:4]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][S:7]2=[O:22])[CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 108762Thiosulfuric acid, disodium salt, monohydrateHCID 105665171'-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4'-piperidine]HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxideYield 133.9%

Reagents, catalysts & solvents 3

HCID 180
Acetone
Solvent
HCID 962WaterSolvent3×
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

10.0 g of the crude tert-butyl spiro[benzo[c]thiophene-1(3H),4′-piperidine]-1′-carboxylate, obtained in Example 1, were added to 50 ml of methylene chloride and 150 ml of acetone followed by cooling to 0 to 5° C. A solution of 15.0 g (24.4 mmol) of Oxone™ in 75 ml of water was dropped in at 5° C. or lower followed by stirring for 3 hours at 0 to 5° C. A solution of 1.72 g (9.8 mmol) of sodium thiosulfate-hydrate in 50 ml of water was added followed by stirring for 30 minutes at 20 to 25° C. 100 ml of methylene chloride and 100 ml of water were then added followed by separation of the aqueous layer. After washing the organic layer with 100 ml of water, it was dried with anhydrous magnesium sulfate followed by distilling off the solvent to obtain 10.5 g of tert-butyl spiro[benzo[c]thiophene-1-(3H),4′-piperidine]-1′-carboxylate 2-oxide as a white foamy substance (crude yield: 100%).

Workup

  1. stirringby stirring for 30 minutes at 20 to 25° C
  2. customfollowed by separation of the aqueous layer
  3. washAfter washing the organic layer with 100 ml of water, it
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-ce8b6c2d5796476bb29c33727972adc0
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07396930B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes