Reacción #1544501

Ecuación de reacción

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

Rendimiento 96.7%

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

Rendimiento 96.7%

Disolventes

dichloro-methane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated under reduced pressure
2. 2
   Otroto remove the solvent
3. 3
   workup.ADDITIONto the residue were added water and toluene
4. 4
   Otrothe insoluble materials were removed by filtration
5. 5
   OtroThe toluene layer was collected
6. 6
   Lavadowashed successively with 1N aqueous sodium hydroxide solution, water
7. 7
   Secadoa saturated aqueous sodium chloride solution, an dried over anhydrous sodium sulfate
8. 8
   ConcentraciónThe resultant was concentrated under reduced pressure
9. 9
   Otroto remove the solvent
10. 10
    Otrothe 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
    Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente