Stannous chloride dihydrate → 1-Benzyl-4-(3-chlorophenyl)pyrrolidin-3-amine

HRID 910440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910440
[CH2:1]([N:8]1[CH2:12][CH:11]([N+:13]([O-])=O)[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[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[CH2:9][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH:11]([NH2:13])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67218087(3SR,4RS)-1-Benzyl-3-(3-chloro-phenyl)-4-nitro-pyrrolidine

Produkt 1

HCID 672180701-Benzyl-4-(3-chlorophenyl)pyrrolidin-3-amineAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of (3SR,4RS)-1-benzyl-3-(3-chloro-phenyl)-4-nitro-pyrrolidine (6.30 g, 19.8 mmol) in EtOAc (150 ml) was added portion wise SnCl2.2H2O (22.43 g, 99 mmol). The reaction mixture was then heated at reflux for 4 hours, cooled down to RT and a saturated aqueous solution of NaHCO3 (500 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. A column chromatography (CH2Cl2/MeOH 95/5) gave 4.47 g (78%) of the title compound as a light yellow oil. ES-MS m/e: 287.0 (M+H+).

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 4 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-7897826759b240f08b4c8222078faeb2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022099B2

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