Synthesis of 1′,3′-Dioxolan-2′-one by the Reaction of Steroidal Oxiranes with Carbon Dioxide: Synthesis of Five-Membered Cis Cyclic Carbonates

Abstract

The reaction of 3β-acetoxy-5,6α-epoxy-5α-cholestane 1, its 3β-chloro analogue 2, and 5,6α-epoxy-5α-cholestane 3 with carbon dioxide gas in the presence of sodium bromide as catalyst with continuous stirring at 100 °C for 30 min affords selectively the corresponding 1′,3′,-dioxolan-2′-ones (steroidal cyclic cis-carbonates) 4–6 in excellent yields. The structures of these products have been established on the basis of their elemental analysis and spectral data (infrared, ¹H NMR, and mass).

Keywords:

• Carbon dioxide
• dimethyl formamide
• dioxolan-2′-one (dioxolanone)
• sodium bromide
• steroidal epoxide

ACKNOWLEDGMENTS

The authors thank the chairman, Department of Chemistry, for providing the necessary facilities. Thanks are also due to the UGC, New Delhi, for a Major Research Project No. UGC-Scheme F.No. 33-263/2007 (SR).