N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine → 2,3-Dihydroxybutanedioic Acid

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Reaction Steps

A solution of (2S,3S) (-) tartaric acid (160.3 g in water (50 ml) was treated with N-methyl-1,2,3,4-tetrahydro-1-naphthylamine (172.2 g), the temperature being allowed to rise to 35° C. The resulting clear solution was chilled to induce crystallisation and granulated for several hours at 5° C. Filtration, washing with water (3×50 ml) and drying gave the crude (-) tartaric acid salt of the (S)-amine (198.2 g) as a white solid, m.p. 99°-106° C. Fractional recrystallisation from water gave the (-)tartaric acid salt of the title compound (59.3 g, 33.7% overall based on available enantiomer) as white crystals, m.p. 107°-109° C., [α]D -12.4° (c=4.96, water). Found: C,54.82; H,7.09; N,4.21. C15H21NO6 ;H2O requires C,54.70; H,7.04; N,4.25%.

Provenance & Evidence