Reacción #6843

Ecuación de reacción

iodomethane

indole

6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester

potassium tert-butoxide

18-crown-6

→

9-methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester

Rendimiento 41.9%

Disolventes

ethyl ether

ethyl ether

ethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solids were removed by filtration
2. 2
   Otrothe solvent was evaporated

Procedimiento

A solution of 6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (175 mg, 0.39 mmol) in 3 mL of ethyl ether was added to a vigorously stirring solution of potassium tert-butoxide (263 mg) and 18-crown-6 (16 mg) in 10 mL ethyl ether. After 10 min, iodomethane (73 uL) in 0.5 mL of ethyl ether was added to the indole solution and the resulting mixture was stirred for 2 h. The solids were removed by filtration and the solvent was evaporated. Silica gel chromatography (10% ethyl acetate in hexanes) gave 9-methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (75 mg).

Fuente