Water → Tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411289Notes

Reaction equation

HRID 1411289 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:13]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[CH2:12][N:11](C(OCC[Si](C)(C)C)=O)[C:8]2=[CH:9][CH:10]=1)(=[O:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:13]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[CH2:12][NH:11][C:8]2=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 904496081-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 90449944Tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylateYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (133 mg, 0.27 mmol) was dissolved in tetrahydrofuran (3 mL). Thereafter, tetra-n-butylammonium fluoride (1 M tetrahydrofuran solution, 0.5 mL) was added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 1 hour. Thereafter, water 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=1:4) to obtain tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (102 mg, quant.) 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=1:4)

Sources & evidence

ORD record
ord-4534c0b5c1a041658ae75b7865881b3e
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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