m-Nitroacetophenone → HCID 131736797, Verbindung

HRID 1486695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486695
[CH:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)=O.[BH4-].[Na+]>CO>[CH:1]1([NH:7][C:8]([CH:10]2[CH2:11][CH2:12][N:13]([CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)[CH3:16])[CH2:14][CH2:15]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 8494m-NitroacetophenoneHCID 4311764Sodium borohydrideHCID 12410238n-Cyclohexylpiperidine-4-carboxamide

Produkt 1

HCID 131736797HCID 131736797, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Piperidine-4-carboxylic acid cyclohexylamide (1.5 g 7.132 mmol) and 3-nitroacetophenone (1.77 g, 10.7 mmol) are dissolved in MeOH (40 mL). Tetraisopropyl-orthotitanate (3.167 mL, 10.7 mmol) is added and the mixture is stirred at RT for 18 h. NaBH4 (539.6 mg, 14.3 mmol) is added carefully. The mixture is evaporated under reduced pressure. DCM (25 mL) and water (25 mL) are added, following by 1 M NaOH solution (50 mL). The organic phase is separated and the aqueous phase is extracted with DCM (25 mL). The combined organic phases are dried over MgSO4, filtered and concentrated. The crude residue is purified by flash chromatography on silica gel using a gradient of heptane/EtOAc 4:1 to EtOAc 100%. After concentration of the product-containing fractions, the title compound (0.375 g, 15%) is obtained as a colorless solid LC-MS A: tR=0.64 min; [M+H]+=360.26.

Aufarbeitung

  1. additionTetraisopropyl-orthotitanate (3.167 mL, 10.7 mmol) is added
  2. customThe mixture is evaporated under reduced pressure
  3. additionDCM (25 mL) and water (25 mL) are added
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted with DCM (25 mL)
  6. dry with materialThe combined organic phases are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue is purified by flash chromatography on silica gel using a gradient of heptane/EtOAc 4:1 to EtOAc 100%

Quellen und Nachweise

ORD-Eintrag
ord-40ff7817415c40428cd748c90186e540
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428456B2

Notizen zur Reaktion

Wird geladen…