Synthesis of 6-Methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline

Abstract

A convenient, larger-scale preparation of 6-methoxy-2-methyl-l,2,3,4-tetrahydro-β-carboline, an alkaloid occurring in the pasture grass, Phalavis tuberosa L., is described. DL-5-Methoxytryptophan is condensed with formaldehyde and the product, DL-6-methoxy-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, treated with dichromate to form 6-methoxy-β-carboline. The methiodide of this base is reduced with borohydride to the required alkaloid in c.60% overall yield.