Reaktion #1544501

Reaktionsgleichung

1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalene-acetic acid

pyrrolidine

benzotriazol-1-yloxy-tris(dimethyl-amino) phosphonium hexafluorophosphate

triethylamine

→

desired compound

Ausbeute 96.7%

1-[(1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalenyl)-acetyl]pyrrolidine

Ausbeute 96.7%

Lösungsmittel

dichloro-methane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated under reduced pressure
2. 2
   Sonstigeto remove the solvent
3. 3
   workup.ADDITIONto the residue were added water and toluene
4. 4
   Sonstigethe insoluble materials were removed by filtration
5. 5
   SonstigeThe toluene layer was collected
6. 6
   Waschenwashed successively with 1N aqueous sodium hydroxide solution, water
7. 7
   Trocknena saturated aqueous sodium chloride solution, an dried over anhydrous sodium sulfate
8. 8
   EinengenThe resultant was concentrated under reduced pressure
9. 9
   Sonstigeto remove the solvent
10. 10
    Sonstigethe residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate=10:1)
11. 11
    workup.ADDITIONthe fractions containing the desired compound
12. 12
    Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalene-acetic acid (8.0 g), pyrrolidine (3.8 g) and benzotriazol-1-yloxy-tris(dimethyl-amino) phosphonium hexafluorophosphate (BOP Reagent,16.7 g) in dichloro-methane (80 ml) was added dropwise triethylamine (3.8 g) at 25° C., and the mixture was stirred for three hours. The mixture was concentrated under reduced pressure to remove the solvent, and to the residue were added water and toluene, and the insoluble materials were removed by filtration. The toluene layer was collected, washed successively with 1N aqueous sodium hydroxide solution, water and a saturated aqueous sodium chloride solution, an dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate=10:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (9.5 g) as an oily product.

Quelle