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CID 16711988 → Tert-butyl 5-fluorospiro[indoline-3,3'-piperidine]-1'-carboxylate

HRID 529090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 529090
[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[C:9](=O)[NH:8][C:5]2=[CH:6][CH:7]=1.COCCO[Al]OCCOC.[Na]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1
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Komponenten

4

Edukt 2

HCID 16711988CID 16711988HCID 23500714Tert-butyl 5-fluoro-2-oxospiro[indoline-3,3'-piperidine]-1'-carboxylate

Produkt 1

HCID 69811766Tert-butyl 5-fluorospiro[indoline-3,3'-piperidine]-1'-carboxylateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred solution of tert-butyl 5-fluoro-2-oxospiro[indoline-3,3′-piperidine]-1′-carboxylate (0.80 g, 2.5 mmol) in toluene (20 mL) was added dropwise a solution of sodium bis(2-methoxyethoxy)aluminium hybrid (Red-Al) in toluene (65% w/w, 1.1 mL, 3.5 mmol) at about 70° C. under N2. The reaction mixture was stirred at about 75° C. for 3 h. After cooling, the reaction mixture was quenched with EtOAc and concentrated in vacuo. The residue was diluted with EtOAc, washed with water and brine, dried and concentrated. The residue was purified by column chromatography (hexane:EtOAc, 3:1) to give tert-butyl 5-fluorospiro[indoline-3,3′-piperidine]-1′-carboxylate (0.18 g, 24%) as an oil. LCMS (APCI+) m/z 307 [M+H]+; Rt=3.66 min.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture was quenched with EtOAc
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washwashed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (hexane:EtOAc, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f1feb520ab654c31bffa9140c7af3f58
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346805B2

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