Sodium Carbonate → (7RS,8aSR)-7-(4-Fluorophenoxy)methyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 1594566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594566
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][CH2:21][CH:22]2[CH2:30][N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:24]3[CH2:23]2)=[CH:18][CH:17]=1>C(O)CC(C)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH:22]2[CH2:30][N:25]3[CH2:26][CH2:27][N:28]([C:2]4[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=4)[CH2:29][CH:24]3[CH2:23]2)=[CH:31][CH:32]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 276852,5-DichloropyridineHCID 20682345(7RS,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

Produkt 1

HCID 9841887(7RS,8aSR)-7-(4-Fluorophenoxy)methyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineAusbeute 2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31260Isoamyl AlcoholLösungsmittel

Versuchsvorschrift

A mixture of 3.8 g (26 mmol) of 2,5-dichloropyridine, 1.3 g (12 mmol) of sodium carbonate, 1.3 g (5.2 mmol) of (7RS,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 2), and 20 mL of isoamyl alcohol was heated at reflux for 18 hours. The solvent was evaporated, the residue taken up in water and ethyl acetate, and the pH adjusted to 11 with sodium carbonate. The layers were separated and the organic phase was dried (magnesium sulfate), filtered, and evaporated. Purification by medium pressure silica gel chromatography with ethyl acetate gave 35 mg (2%) of the title compound. Mp (.HCl) 202-206° C. HRMS calc'd for C19H21ClFN3O (MH+): 362.1435, found: 362.1451.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. customThe layers were separated
  5. dry with materialthe organic phase was dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by medium pressure silica gel chromatography with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1b3e0315bc9c4adc84ebffb4c8244da8
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284757B1

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