Nitrogen → 8-[4-(6-(2,5-Dimethylpyrrolyl)-pyridin-2-yl)-phenyl]-3-benzyl-3-aza-bicyclo[3.2.1]octan-8-ol

HRID 1977916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977916
N#N.Br[C:4]1[N:9]=[C:8]([C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][C:11]=2[CH3:16])[CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[CH2:22]([N:29]1[CH2:35][CH:34]2[C:36](=[O:37])[CH:31]([CH2:32][CH2:33]2)[CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>O1CCCC1>[CH3:16][C:11]1[NH:12][C:13]([CH3:15])=[CH:14][C:10]=1[C:8]1[N:9]=[C:4]([C:40]2[CH:39]=[CH:38][C:43]([C:36]3([OH:37])[CH:34]4[CH2:33][CH2:32][CH:31]3[CH2:30][N:29]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:35]4)=[CH:42][CH:41]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 947NitrogenHCID 8058HexaneHCID 156391343-Benzyl-3-azabicyclo(3.2.1)octan-8-oneHCID 543198942-(2,5-Dimethylpyrrolyl)-6-bromopyridineHCID 178418339Butyllithium

Produkt 1

HCID 543978948-[4-(6-(2,5-Dimethylpyrrolyl)-pyridin-2-yl)-phenyl]-3-benzyl-3-aza-bicyclo[3.2.1]octan-8-olAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a 125 mL 3-necked round-bottomed flask equipped with septum and N2 inlet were added 1.86 g (5.70 mmol) 6-bromo-2-(2,5-dimethylpyrrolyl)-pyridine and 40 mL dry tetrahydrofuran. The solution was cooled to −60° C., and 2.73 mL (6.84 mmol) of a 2.5M solution of butyl lithium in hexane was added dropwise and the solution stirred 10 min at −60° C. Then a solution of 1.47 g (6.84 mmol) 3-benyl-3-aza-bicyclo[3.2.1]octan-8-one in 15 mL dry tetrahydrofuran was added dropwise, and the reaction stirred at −60° C. for 10 minutes, and then at room temperature for 3 hours. The reaction was quenched with aqueous ammonium chloride solution and taken up in ethyl acetate. The organic layer was separated and washed with more aqueous ammonium chloride solution and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methanol and methylene chloride to afford 413 mg (16%) of a yellow oil which solidified, mp 58-68° C.

Aufarbeitung

  1. stirringthe reaction stirred at −60° C. for 10 minutes
  2. waitat room temperature for 3 hours
  3. customThe reaction was quenched with aqueous ammonium chloride solution
  4. customThe organic layer was separated
  5. washwashed with more aqueous ammonium chloride solution and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ba9286a0262640c59b169e46a17c90e4
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235750B1

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