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An efficient and scalable process for the synthesis of 19-hydroxyprogesterone was obtained through seven steps with 34.5% total yield, which is much higher than the process reported in the literature (11.0% total yield). The plausible ring-opening mechanism of 6,19-epoxy bridge in compound  7  was first proposed and the structures of intermediates were supported by the LC-MS analysis of the reaction mixture.

Synthesis of 19-hydroxyprogesterone and insights into the ring-opening mechanism of the 6,19-epoxy bridge