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

HRID 747492Notes

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

Participants

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

stirringby stirring for 30 minutes at 20 to 25° C
customfollowed by separation of the aqueous layer
washAfter washing the organic layer with 100 ml of water, it
dry with materialwas dried with anhydrous magnesium sulfate
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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