HCID 90354850, compound → Estetrol

HRID 878797Notes

Reaction equation

HRID 878797 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([O:23]C(=O)C)[C@@H:13]([OH:27])[C@H:12]4[OH:28])[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.C(OC1C=CC2[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)[C@H](OC(=O)C)[C@H](O)[C@@H]4O)CCC=2C=1)(=O)C>CO>[CH3:16][C@@:15]12[C@@H:14]([OH:23])[C@H:13]([OH:27])[C@H:12]([OH:28])[C@H:11]1[C@@H:10]1[CH2:9][CH2:8][C:7]3[CH:6]=[C:5]([OH:4])[CH:22]=[CH:21][C:20]=3[C@H:19]1[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 90354850HCID 90354850, compoundHCID 131732616HCID 131732616, compound

Product 1

HCID 27125Estetrol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%.

Workup

  1. customThese compounds were isolated by thin layer chromatography

Sources & evidence

ORD record
ord-65c7d4366f584f438391f0e35fcc07c0
Source dataset
uspto-grants-2015_03
Patent number
US08987484B2

Reaction notes

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