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Water → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411309
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1411309
[CH:1]([C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+].O>C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 904497561-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-formylspiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Produkt 1

HCID 904495331-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-formylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (553 mg, 1.24 mmol) was dissolved in ethanol (12 mL). Thereafter, sodium borohydride (76.0 mg, 2.01 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 30 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with chloroform. 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=5:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (473 mg, 85%) in the form of a light yellow solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-164618ebee45469b8dd96dbdd4a04472
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08921576B2

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