StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Ammonium Chloride → Racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065417
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2065417
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][CH2:7][CH2:8][C:9]([CH3:28])([CH3:27])[CH2:10][CH:11]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])[CH2:12][N+:13]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.[Zn]>[NH2:13][CH2:12][CH:11]([CH:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])[CH2:10][C:9]([CH3:28])([CH3:27])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:30])[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 58399000Racemic 3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dim ethyl-1-nitromethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one

Produkt 1

HCID 58398996Racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of racemic 3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-1-nitromethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one (0.5 g, 1.1 mmol) in methanol (20 mL) was added an aqueous solution (5 mL) of ammonium chloride (0.6 g, 11 mmol), followed by the addition of Zinc (Aldrich, activated) (0.7 g, 11 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to a small volume, then the residue was partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated to give racemic 3-[1-aminomethyl-5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl]-6-chloro-1,3-dihydro-indol-2-one as a white foam (0.4 g, 86%)

Aufarbeitung

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated to a small volume
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-31ee84f9591544d19adf5947e920149f
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288431B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion