(1<i>RS</i>,2<i>RS</i>,6<i>RS</i>)-2-(6-Amino-9<i>H</i>-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol Dihydrochloride

Abstract

The title compound (1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride was synthesized for the first time in two steps, the first of which was a regioselectivity of epoxide ring-opening reaction under the action of adenine, yielding N-tert-butoxycarbonyl-((1RS,2RS,6RS)-2-(6-amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol. By treating the latter with a saturated methanolic solution of hydrogen chloride, it was possible to obtain ((1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride. The features of the molecular and crystal structure of ((1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol dihydrochloride are discussed based on X-ray diffraction studies. The product overall yield was 40% out of two steps and after purification by column chromatography and recrystallization. The product was characterized by 1H-NMR, 13C-NMR, IR spectroscopy, HRMS and X-ray.

Keywords

• nitrogen heterocycles
• spiro compound
• adenine
• ring-opening reaction