Citric Acid → (R)-6-Amino-alpha-[[(1(R)-methyl-2-(1H-indol-3-yl)ethyl)amino]methyl]-3-pyridinemethanol Citrate

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Reaction Steps

A solution of 0.5 g of this tetrazole in 15 ml of methanol is treated with 0.6 g of SnCl2.2H2O for 5 hours at reflux under nitrogen. The reaction mixture is partially concentrated and then poured into a mixture of 25 ml of CH2Cl2 and 15 ml of 1N NaOH solution. The layers are separated and the aqueous layer further extracted with CH2Cl2. The combined organic phases are backwashed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. Concentration of this solution and chromatography on silica gel affords the product which is dissolved in ethanol and treated with one equivalent of an ethanolic solution of citric acid. The mixture is aged for approximately one hour and the citrate salt is collected by filtration.

Provenance & Evidence