Methanol → 1-Acetamido-4-bromo-2-nitro-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

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Reaction Steps

A mixture of 1-acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene (0.3 g) in trifluoroacetic acid (10 mL) was cooled in an icebath and treated with fuming nitric acid (0.5 mL). After stirring for 4 h, the solvent was evaporated and the residue taken up in methylene chloride:water. The mixture was basified with 12.5% NaOH, and the aqueous layer back extracted. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a solid. Preparative thin layer chromatography (7:3 EtOAc:MeOH) was used to obtain the purified product (0.12 g).

Provenance & Evidence