Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HCID 90354850 | HCID 90354850 | — |
| Reactant | HCID 131732616 | HCID 131732616 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Estetrol | HCID 27125 | — |
Reaction Steps
The carbonyl group at C17 of the 3-hydroxyestetra-1,3,5(10),15-tetraen-17-one was reduced with LiAlH4 to estra-1,3,5(10),15-tetraene-3,17-diol that was isolated as the diacetate (compound B). Compound B was subjected to cis-hydroxylation of the double bond of D ring by using Osmium tetraoxyde which resulted into the formation of estra-1,3,5(10)-triene-3,15α,16α,17α-tetraol-3,17-diacetate (compound C) as the major product associated with estra-1,3,5(10)-triene-3,15β,16β,17β-tetrol-3,17 diacetate. These compounds were isolated by thin layer chromatography. Compound C under heating with K2 CO3 in methanol produces estetrol (compound D) (Scheme 1). The overall yield of this three step process was, starting from estrone 3-hydroxyestetra-1,3,5(10),15-tetraen-17-one, only about 7%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08987484B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-65c7d4366f584f438391f0e35fcc07c0 |
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| Source note | uspto-grants-2015_03 |
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