3-Chloro-2-methyl-1-propene → (+)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(2-methylprop-2-enyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

5.7 g. (18.07 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline and 3.7 g. (44 mmol) sodium bicarbonate in 120 ml. ethanol are mixed with 1.76 ml. (1.64 g., 18,07 mmol) 3-chloro-2-methylprop-1-ene. The mixture is allowed to react for 30 minutes at ambient temperature and thereafter for 3 hours at 80° C., while stirring. The usual working up and chromatographic purification on silica gel with chloroform as elution agent gives (+)-7-hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(2-methylprop-2-enyl)-1,2,3,4-tetrahydroisoquinoline in the form of a TLC-uniform yellowish foam.

Provenance & Evidence