Tributylstannane → HCID 67932254, compound

HRID 868171Notes

Reaction equation

[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@:22](Br)([C@@H:23]([OH:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[CH:18]=[CH:19]2)[C@@H:14]([CH3:30])[CH2:13]3)[CH2:10][C@@H:9]1[CH3:31])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C@@H:23]([OH:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[CH:18]=[CH:19]2)[C@@H:14]([CH3:30])[CH2:13]3)[CH2:10][C@@H:9]1[CH3:31])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 5948Tributylstannane

HCID 70407511HCID 70407511, compound

Product 1

HCID 67932254HCID 67932254, compoundYield 45.6%

Procedure

300 mg of 17α-acetoxy-9α-bromo-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione is debrominated as described in Example 1(E) with tributyltin hydride, worked up, and purified, thus isolating 115 mg of 17α-acetoxy-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione, mp 270°-272° C.

Workup

custompurified

Sources & evidence

ORD record: ord-e38bf31dab084034ae43f3307f1454ab
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04777165

Reaction notes

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