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

HRID 1411289노트

반응식

HRID 1411289 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4534c0b5c1a041658ae75b7865881b3e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921576B2

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