Hydrofluoric Acid → HCID 15611582, compound

HRID 1198862Notes

Reaction equation

[O:1]1[C@@H:21]2[C@:2]31[C@H:11]([C@H:12]1[C@:19]([CH3:22])([CH2:20]2)[C@@:15]([OH:23])([C:16](=[O:18])[CH3:17])[C@H:14]([CH3:24])[CH2:13]1)[CH2:10][C@H:9]([F:25])[C:8]1[C@:3]3([CH3:27])[CH2:4][CH2:5][C:6](=[O:26])[CH:7]=1.[FH:28]>>[F:25][C@@H:9]1[C:8]2[C@:3]([CH3:27])([CH2:4][CH2:5][C:6](=[O:26])[CH:7]=2)[C@:2]2([F:28])[C@H:11]([C@H:12]3[C@:19]([CH3:22])([CH2:20][C@@H:21]2[OH:1])[C@@:15]([OH:23])([C:16](=[O:18])[CH3:17])[C@H:14]([CH3:24])[CH2:13]3)[CH2:10]1

Participants

Reactant 2

HCID 14917Hydrofluoric Acid

HCID 15611580HCID 15611580, compound

Product 1

HCID 15611582HCID 15611582, compound

Procedure

The epoxide ring of the 9β,11β-epoxy-6α-fluoro-17α-hydroxy-16α-methyl-4-pregnene-3,20-dione is opened by means of hydrogen fluoride, and 6α,9α-difluoro-11β,17 -dihydroxy-16α-methyl-4-pregnene-3,20-dione is obtained. The conditions under which this reaction step is performed are also conventional (J. Fried et al. Organic Reactions in Steroid Chemistry, van Nostrand Reinhold Co., New York et al., Vol. 1, 1972, 425 ff).

Sources & evidence

ORD record: ord-66fd9441030b409397e1be50dc4d6a74
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898693

Reaction notes

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