Reacción #2235

Ecuación de reacción

Acetyl chloride

methanol

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

→

title compound

Rendimiento 46.6%

3-Methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline

Rendimiento 46.6%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas then continued for a further 24 h
5. 5
   OtroThe solvent was removed in vacuo
6. 6
   workup.ADDITIONdichloromethane was added
7. 7
   Otrothe solid thus formed
8. 8
   Filtraciónwas filtered off
9. 9
   Otropartitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
10. 10
    SecadoThe organic phase was dried (magnesium sulphate)
11. 11
    Filtraciónfiltered
12. 12
    Otrothe filtrate evaporated in vacuo

Procedimiento

Acetyl chloride (0.88 g) was added to methanol (100 ml) with stirring at 0° C. After 10 minutes, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (J. Am. Chem. Soc., 1962, 48, 4487-4494) (2.0 g) was added; the reaction was allowed to warm to room temperature and stirred overnight. DMF (1 ml) was then added and stirring was then continued for a further 24 h. The solvent was removed in vacuo; dichloromethane was added and the solid thus formed was filtered off and partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml). The organic phase was dried (magnesium sulphate), filtered, and the filtrate evaporated in vacuo to yield the title compound as a pale yellow oil (1.0 g).

Fuente