6-Nitroindoline → 1-(1-Methyl(4-piperidyl))-6-nitroindoline

HRID 238503

Reaktionsgleichung

Reaktionsgleichung von HRID 238503
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C.CC(O)=O>[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=3)[CH2:8][CH2:9]2)[CH2:16][CH2:15]1

Komponenten

7

Edukt 4

HCID 297576-NitroindolineHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 187966231-(1-Methyl(4-piperidyl))-6-nitroindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h. The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc'd. for C14H19N3O2—261.32.

Aufarbeitung

  1. stirringstirred for 1 h
  2. customThe resulting mixture was separated by separation funnel
  3. extractionthe organic layer was extracted once with saturated NaHCO3 solution and once with brine
  4. dry with materialThe resulting organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography on silica gel with 2:1 EtOAc
  8. customMeOH to afford an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-7d1fd85e774f4ec59f2291df1b4171fd
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642624B2

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