Stannous chloride dihydrate → 1-Benzyl-4-phenylpyrrolidin-3-amine

HRID 910447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910447
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([N+:19]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([NH2:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine

Produkt 1

HCID 433170851-Benzyl-4-phenylpyrrolidin-3-amineAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of (3RS,4SR)-1-benzyl-3-nitro-4-phenyl-pyrrolidine (1.0 g, 3.54 mmol) in EtOAc (50 ml) was added in one portion SnCl2.2H2O (3.99 g, 17.70 mmol). The reaction mixture was then heated at reflux for 2 hours, cooled down to RT and a saturated aqueous solution of NaHCO3 (100 ml) was added. The salts were filtered off and the product extracted with EtOAc. The organic phases were then dried over Na2SO4, and concentration under vacuum gave 0.72 g (80%) of (3RS,4SR)-1-benzyl-4-phenyl-pyrrolidin-3-ylamine as a light yellow oil. The product was then used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe salts were filtered off
  4. extractionthe product extracted with EtOAc
  5. dry with materialThe organic phases were then dried over Na2SO4, and concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b22a60d50fb9480d825cc8b6e8fab3a9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022099B2

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