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

HRID 1411289ノート

反応式

HRID 1411289 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4534c0b5c1a041658ae75b7865881b3e
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

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