Water → Methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-imidazole-5-carboxylate

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Reaction Steps

4.3 Parts of 1,1-dimethylethyl nitrite were dissolved in 40 ml N,N-dimethylformamide and heated to +60° C. A solution of 8 parts of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate in 50 ml N,N-dimethylformamide was dropwise added at +60° C. After 1.5 hour the solution was poured into water and extracted with ethyl acetate. The organic phase was dried with Na2SO4, filtered and concentrated. The resulting 8.5 parts of crude material were chromatographed on a silica gel column with an ethyl acetate/hexane mixture (1:1). 2.9 Parts (38%) of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-imidazole-5-carboxylate, mp. 151°-152° C. (compound 2.2), were obtained. According to 1H-NMR the product consists of an epimeric mixture of 2 isomers.

Provenance & Evidence