Reacción #339060

Ecuación de reacción

hydrochloric acid

sarcosine methyl ester hydrochloride

triethylamine

4-Nitrophenyl[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate

→

title compound

3-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-1-methylimidazolidine-2,4-dione hydrochloride

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 5 h
2. 2
   Temperaturarefluxed for 2 h
3. 3
   Concentraciónthe reaction mixture was concentrated
4. 4
   OtroAfter separation of the phases
5. 5
   Lavadothe organic phase was washed five times with saturated potassium carbonate solution
6. 6
   SecadoDrying over magnesium sulfate and filtration
7. 7
   Concentraciónwere followed by concentration
8. 8
   OtroThe residue was purified by means of preparative HPLC
9. 9
   Otrothe acetonitrile was removed on a rotary evaporator
10. 10
    Extracciónextracted three times with ethyl acetate
11. 11
    SecadoAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
12. 12
    Filtraciónwere filtered
13. 13
    Concentraciónconcentrated to dryness
14. 14
    Otrofreeze-dried

Procedimiento

4-Nitrophenyl[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate (125 mg) was dissolved in absolute THF (5 ml), and sarcosine methyl ester hydrochloride and triethylamine were added dropwise with stirring. After stirring for 5 h, the reaction mixture was freed of the solvent, and the residue was admixed with water and 2 N hydrochloric acid and refluxed for 2 h. After standing overnight, the reaction mixture was concentrated and admixed with ethyl acetate, water and saturated potassium carbonate solution. After separation of the phases, the organic phase was washed five times with saturated potassium carbonate solution and twice with saturated sodium chloride solution. Drying over magnesium sulfate and filtration were followed by concentration. The residue was purified by means of preparative HPLC. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with saturated potassium carbonate solution and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. The residue was taken up with water/hydrochloric acid and freeze-dried. 60 mg of the title compound were obtained.

Fuente