Sodium Thiosulfate → HCID 90449581, compound

HRID 1411286Notes

Reaction equation

HRID 1411286 reaction equation
[N:1]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:5][CH2:4][C:3]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:6]2)[CH2:2]1.[Br:30]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(C)(C)C.O>[Br:30][C:11]1[CH:12]=[C:13]2[C:3]3([CH2:4][CH2:5][N:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:2]3)[CH2:6][N:7]([C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:20])[CH3:21])=[O:15])[C:8]2=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 90449612HCID 90449612, compound

Product 1

HCID 90449581HCID 90449581, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (15.2 g, 36.5 mmol) was dissolved in t-butanol (240 mL) and water (40 mL). Thereafter, N-bromosuccinimide (7.9 g, 44.4 mmol) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred at 60° C. for 15 hours. Thereafter, an aqueous solution of sodium thiosulfate was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (12.9 g, 71%) in the form of a white amorphous product.

Workup

  1. extractionthe mixed solution was then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-635cbadfdb304faa9593691696b2a282
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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