1,2,3,4-Tetrahydroisoquinoline → 2-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

1,2,3,4-tetrahydroisoquinoline (25.0 g) was dissolved in acetonitrile (100 ml), and sodium carbonate (40.0 g) and epibromohydrin (31.0 g) were added thereto. Then, the mixture was heated under reflux for 4 hours. After separating salts in the mixture by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Wako gel C-200, 500 g), and then was eluted with a mixed solvent of 99 parts of chloroform and 1 part of methanol to obtain 2-{1-(2,3-epoxy) propyl}-1,2,3,4-tetrahydroisoquinoline (15.6 g).

Provenance & Evidence