A new highly efficient method for the synthesis of trans-tetrahydro-3,4-furandiamine

A new four-step, highly efficient synthesis of trans-tetrahydro-3,4-furandiamine is described. Nitromercuration of 2,5-dihydrofuran with sodium nitrite and mercuric chloride in aqueous solution followed by base catalyzed elimination yielded 3-nitro-2,5-dihydrofuran which was aminated with ammonium hydroxide to give trans-tetrahydro-4-nitro-3-furanamine. Catalytic reduction of this material afforded the desired product 5 in 37% overall yield.