Sodium Hydroxide → 3-(3,4-Dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene

HRID 987582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987582
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2(O)[CH2:15][CH:14]3[N:16]([CH3:17])[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].O=S(Cl)Cl.[OH-].[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH:11]3[N:16]([CH3:17])[CH:14]([CH2:13][CH2:12]3)[CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 180091653-(3,4-Dichlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

Produkt 1

HCID 102210203-(3,4-Dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-eneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To 2.35 g (8.76 mmol) of 3-(3,4-dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol in 50 mL of Cl(CH2)2Cl is added 1.92 mL (3.13 g, 26.67 mmol) SOCl2. After stirring at 23 C for 17 h, the reaction mixture is poured into 5 N NaOH, extracted with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered and extracted to give a brown oil. Flash chromatography on SiO2, eluting with CHCl3/MeOH (40/1 to 10/1) gives 1.24 g (4.62 mmol, a 53% yield) of the title compound as an orange oil. MS (ES) m/z 269 (MH)+.

Aufarbeitung

  1. extractionextracted with 1×100 mL H2O, 1×100 mL brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. extractionextracted
  5. customto give a brown oil
  6. washFlash chromatography on SiO2, eluting with CHCl3/MeOH (40/1 to 10/1)
  7. customgives 1.24 g (4.62 mmol

Quellen und Nachweise

ORD-Eintrag
ord-736826d272d54880a0908640d78a87cc
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632824B2

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